LCD Media

Abstract

To provide a liquid crystal medium with high reliability.SOLUTION: The present invention relates to a liquid crystal medium, comprising one or more compounds of formula I, and one or more other compounds selected from the group of compounds of specific structures. (RL is H, a C1-15 linear or branched alkyl group or a C1-15 linear or branched alkoxy group (where, one or more CH2 groups may each be replaced, independently of one another, by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, -O-CO- or the like in such a way that O atoms are not linked directly to one another); XL is F, Cl, CN, CHF2, CF3, OCF3; YL is H, F, Cl or CH3).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to liquid crystal (LC) media and the use of LC media for optical, electro-optical and electronic purposes, and more particularly to LC displays, especially IPS, FFS, VA, or PS-VA displays. [Background technology]

[0002] One mode of liquid crystal display (LCD) currently in use is the TN ("twisted nematic") mode. However, TN LCDs have the disadvantage of strong contrast dependence on the viewing angle.

[0003] In addition, so-called VA ("vertical alignment") displays with wider viewing angles are known. The LC cells of a VA display contain a layer of LC medium between two transparent electrodes, where the LC medium typically has negative dielectric anisotropy. In the switched-off state, the molecules in the LC layer are oriented perpendicular to the electrode surface (homeotropic) or have a tilt homeotropic orientation. When a voltage is applied to the two electrodes, the LC molecules reorient to be parallel to the electrode surface.

[0004] Furthermore, OCB (optically compensated bend) displays are known, which are based on the birefringence effect and have an LC layer with a so-called "bend" orientation and typically positive dielectric anisotropy. When a voltage is applied, the LC molecules perpendicular to the electrode surface are reoriented. In addition, to prevent undesirable transparency of the bend cells to light in the dark, OCB displays usually include one or more birefringent optical retardation films. Compared to TN displays, OCB displays have a wider viewing angle and a shorter response time.

[0005] Furthermore, there are also known so-called IPS (in-plane switching) displays that contain an LC layer between two substrates, with two electrodes placed on only one of the two substrates, preferably having a comb-like structure with interlocking elements. When a voltage is applied to the electrodes, an electric field with a significant component parallel to the LC layer is generated between the electrodes. As a result, reorientation of LC molecules occurs within the layer plane.

[0006] Furthermore, so-called FFS ("fringe field switching") displays have been reported (see especially SHJung et al., Jpn.J.Appl.Phys., Vol. 43, No. 3, 2004, p. 1028; Non-Patent Literature 1), which contain two electrodes on the same substrate, with one electrode structured in a comb-like manner and the other unstructured. This generates a strong so-called "fringe field," that is, a strong electric field near the electrode ends and an electric field having both strong vertical and strong horizontal components throughout the entire cell. FFS displays have low contrast and viewing angle dependence. Typically, FFS displays contain an LC medium with positive dielectric anisotropy and an orientation layer, usually polyimide, which imparts planar orientation to the molecules of the LC medium.

[0007] FFS displays can operate as either active-matrix or passive-matrix displays. In active-matrix displays, individual pixels are typically addressed by integrated nonlinear active elements such as transistors (e.g., thin-film transistors ("TFTs")), while in passive-matrix displays, individual pixels are typically addressed by multiplexing methods as known from the prior art.

[0008] Furthermore, FFS displays have been disclosed that have similar electrode designs and layer thicknesses to FFS displays, but include a layer of LC medium having negative dielectric anisotropy instead of LC medium having positive dielectric anisotropy (see SHLee et al., Appl. Phys. Lett. Vol. 73 (No. 20), 1998, pp. 2882-2883 (Non-Patent Literature 2) and SHLee et al., Liquid Crystals Vol. 39 (No. 9), 2012, pp. 1141-1148 (Non-Patent Literature 3)). Compared to LC medium having positive dielectric anisotropy, LC medium having negative dielectric anisotropy exhibits a preferred director orientation with less tilt and more twisted orientation, and as a result, these displays have higher transmittance. The display further includes an orientation layer, preferably polyimide, provided on at least one substrate, the orientation layer in contact with the LC medium to induce planar orientation of LC molecules in the LC medium. These displays are also known as "Ultra Brightness-FFS (UB-FFS)" mode displays. These displays require highly reliable LC media.

[0009] As used herein, the term "reliability" refers to the performance quality of a display under various stresses such as illumination load, temperature, humidity, and voltage, and includes factors affecting the display such as image fixation (area and linear image fixation), unevenness, and dirt, as is known to those skilled in the art in the field of LC displays. A standard parameter used to classify reliability is typically voltage holding ration (VHR), which is a measure of the constant voltage maintained in a test display. Among other factors, a high VHR is an essential condition for high reliability of an LC medium.

[0010] In more recent types of VA displays, uniform orientation of LC molecules is limited to multiple relatively small domains within the LC cell. Discrinciple may exist between these domains, also known as tilt domains. Compared to conventional VA displays, VA displays with tilt domains have greater contrast and viewing angle independence for midtones (gray shading). In addition, the manufacture of this type of display is simpler because additional treatment of the electrode surface for uniform molecular orientation in the switched-on state, such as rubbing, is no longer required. Instead, the preferred direction of the tilt or pre-tilt angle is controlled by a special design of the electrodes.

[0011] In so-called MVA ("multidomain vertical alignment") displays, this is typically achieved by electrodes with protrusions that produce localized pre-tilt. As a result, when a voltage is applied, LC molecules orient themselves parallel to the electrode surface in different directions within differently defined regions of the cell. This achieves "controlled" switching and prevents the formation of interfering disclination lines. This orientation improves the viewing angle of the display, but results in reduced transparency to light. For further development of MVA, protrusions are used on only one electrode side, while the opposite electrode has a slit, improving transparency to light. When a voltage is applied, the slitted electrode creates a heterogeneous electric field within the LC cell, meaning that controlled switching is still achieved. The distance between the slit and the protrusion can be increased to further improve transparency to light, but this results in longer response times. In so-called PVA (patterned VA), protrusions are completely unnecessary, and both electrodes are structured by slits on opposite sides, resulting in increased contrast and improved light transparency. However, this is technically difficult, and the display becomes sensitive to mechanical influences (such as "tapping"). Nevertheless, in many applications, such as monitors and especially TV screens, there is a demand for reduced display response time and improved contrast and brightness (transparency).

[0012] Further developments involve so-called PS ("polymer sustained") or PSA ("polymer sustained alignment") type displays, for which the term "polymer stabilized" is sometimes used. In these displays, a small amount (e.g., 0.3% by weight, typically less than 1% by weight) of one or more polymerizable compounds, preferably polymerizable monomer compounds, is added to the LC medium. After filling the display with the LC medium, polymerization or crosslinking occurs in situ, usually by UV photopolymerization, while optionally applying a voltage to the display electrodes. Polymerization is carried out at a temperature at which the LC medium exhibits a liquid crystal phase, usually at room temperature. Adding polymerizable mesogens or liquid crystal compounds, also known as reactive mesogens or "RM (reactive mesogen)," to the LC mixture has proven particularly appropriate.

[0013] Unless otherwise indicated, the term "PSA" is used below to refer generally to polymer-maintained orientation type displays, and the term "PS" is used to refer to specific display modes such as PS-VA and PS-TN.

[0014] Furthermore, unless otherwise indicated, the term "RM" will be used below to refer to polymerizable mesogens or liquid crystal compounds.

[0015] For the time being, the PS(A) principle is used in various modes of conventional LC displays. For example, PS-VA, PS-OCB, PS-IPS, PS-FFS, PS-UB-FFS, and PS-TN displays are known. In the case of PS-VA and PS-OCB displays, RM polymerization is preferably carried out with voltage applied, while in the case of PS-IPS displays, it is carried out with or without voltage applied, preferably without voltage. As shown in the test cell, the PS(A) method results in pre-tilt in the cell. For example, in the case of PS-OCB displays, the bend structure can be stabilized, and the offset voltage can be made unnecessary or reduced. In the case of PS-VA displays, pre-tilt has a positive effect on response time. Standard MVA or PVA pixel and electrode layouts can be used for PS-VA displays. In addition, however, it is also possible to operate by structuring only one side of the electrode without providing protrusions, for example, which greatly simplifies manufacturing and at the same time results in very good contrast and very good transparency to light.

[0016] Furthermore, so-called positive VA (positive VA) displays have been proven to be a particularly suitable mode. Similar to classical VA displays, in the initial state without applied voltage, the initial orientation of LC molecules in positive VA displays is homeotropic, i.e., substantially perpendicular to the substrate. However, in contrast to classical VA displays, positive VA displays use an LC medium with positive dielectric anisotropy. Similar to commonly used IPS displays, the two electrodes in a positive VA display are located on only one of the two substrates, preferably exhibiting an interlocking comb-like (interdigital) structure. By applying a voltage to the interdigital electrodes, the electrodes generate an electric field substantially parallel to the layer of LC medium, and the LC molecules are converted to an orientation substantially parallel to the substrate. In addition, in positive VA displays, it has been proven advantageous that adding RM to the LC medium and stabilizing the polymer polymerized within the display can significantly reduce the switch time.

[0017] PS-VA displays are described, for example, in European Patent Application Publication No. 1170626 (Patent Document 1), U.S. Patent No. 6,861,107 (Patent Document 2), U.S. Patent No. 7,169,449 (Patent Document 3), U.S. Patent Application Publication No. 2004 / 0191428 (Patent Document 4), U.S. Patent Application Publication No. 2006 / 0066793 (Patent Document 5), and U.S. Patent Application Publication No. 2006 / 0103804 (Patent Document 6). PS-OCB displays are described, for example, in T.-J.-Chen et al., Jpn.J.Appl.Phys. Vol. 45, 2006, pp. 2702-2704 (Non-Patent Document 4) and SH Kim, L.-C.-Chien, Jpn.J.Appl.Phys. Vol. 43, 2004, pp. 7643-7647 (Non-Patent Document 5). PS-IPS displays are described, for example, in U.S. Patent No. 6,177,972 (Patent Document 7) and Appl. Phys. Lett. 1999, Vol. 75 (No. 21), p. 3264 (Non-Patent Document 6). PS-TN displays are described, for example, in Optics Express 2004, Vol. 12 (No. 7), p. 1221 (Non-Patent Document 7).

[0018] Below the layer formed by the phase-separated and polymerized RM, which induces the aforementioned pre-tilt angle, PSA displays typically include, for example, an orientation layer of polyimide that provides the initial orientation of LC molecules before the polymer stabilization process.

[0019] Rubbed polyimide layers have long been used as orientation layers. However, the rubbing process causes many problems, including unevenness, contamination, electrostatic discharge, and debris. Therefore, it has been proposed to use polyimide layers prepared by photo-oriented ordering, utilizing photo-induced orientation ordering of the orientation surface, instead of rubbed polyimide layers. This can be achieved through photodegradation, photodimerization, or photoisomerization using polarization.

[0020] However, a properly derivatized polyimide layer containing photoreactive groups is still required. Generally, the effort and cost involved in fabricating such a polyimide layer, processing the polyimide, and modifying it with bumps or polymer layers are relatively high.

[0021] In addition, undesirable interactions between the polyimide orientation layer and certain compounds in the LC medium were often observed to lead to a decrease in the electrical resistance of the display. Therefore, when the aim is to improve display parameters such as viewing angle dependence, contrast, and response time by using such LC compounds, the number of suitable and available LC compounds is significantly reduced. Consequently, it was desirable to omit the polyimide orientation layer.

[0022] In some display modes, this is achieved by adding self-aligning agents or additives to the LC medium that induce a desired orientation in situ, such as homeotropic or planar orientation, through a self-assembly mechanism. This allows for the omission of one or both orientation layers on the substrate. These display modes are also called "self-aligned" or "self-aligning" (SA) modes.

[0023] In SA displays, a small amount of self-orienting additive, typically 0.1–2.5%, is added to the LC medium. Suitable self-orienting additives are compounds having, for example, an organic core group and one or more polar anchor groups linked to it, which can interact with the substrate surface to cause orientation of the additive on the substrate surface and induce the desired orientation in the LC molecule. Preferred self-orienting additives include, for example, a mesogenic group and linear or branched alkyl side chains terminated by one or more polar anchor groups selected from, for example, hydroxy, carboxy, amino, or thiol groups. The self-orienting additive may also include one or more polymerizable groups that can be polymerized under conditions similar to those used in RM in the PSA process.

[0024] SA-VA displays and SA-FFS displays have been disclosed to date. In particular, suitable self-orienting additives for inducing homeotropic orientation for use in SA-VA mode displays are disclosed, for example, in U.S. Patent Application Publication 2013 / 0182202 (Patent Document 8), U.S. Patent Application Publication 2014 / 0138581 (Patent Document 9), U.S. Patent Application Publication 2015 / 0166890 (Patent Document 10), and U.S. Patent Application Publication 2015 / 0252265 (Patent Document 11).

[0025] Furthermore, SA mode can be used in combination with PSA mode. Therefore, the LC medium used in such a combined mode display includes both one or more types of RM and one or more types of self-aligning additives.

[0026] Similar to the conventional LC displays described above, PSA displays can operate as either active-matrix or passive-matrix displays. In active-matrix displays, individual pixels are typically addressed by integrated nonlinear active elements such as transistors (e.g., thin-film transistors ("TFTs")), while in passive-matrix displays, as is known from prior art, individual pixels are typically addressed by multiplexing.

[0027] Furthermore, PSA displays may also include an alignment layer on one or both of the substrates forming the display cells. If electrodes are present, the alignment layer is usually coated onto the electrodes so as to come into contact with the LC medium and induce the initial alignment of LC molecules. The alignment layer may contain or consist of polyimide, for example, and may be rubbed, and can be prepared by photoalignment.

[0028] In particular, for monitors and especially television applications, there is a continuing demand for optimizing not only the response time of LC displays but also the contrast and brightness (and thus, the transmittance). Here, the PSA method can offer significant advantages. In particular, for PS-VA, PS-IPS, PS-FFS, and PS-positive-VA displays, it is possible to achieve a reduction in response time in correlation with the measurable pre-tilt in the test cell without significantly adversely affecting other parameters. [Prior art documents] [Patent Documents]

[0029] [Patent Document 1] European Patent Application Publication No. 1170626 [Patent Document 2] U.S. Patent No. 6,861,107 [Patent Document 3] U.S. Patent No. 7,169,449 [Patent Document 4] U.S. Patent Application Publication No. 2004 / 0191428 [Patent Document 5] U.S. Patent Application Publication No. 2006 / 0066793 [Patent Document 6] U.S. Patent Application Publication No. 2006 / 0103804 [Patent Document 7] U.S. Patent No. 6,177,972 [Patent Document 8] U.S. Patent Application Publication No. 2013 / 0182202 [Patent Document 9] U.S. Patent Application Publication No. 2014 / 0138581 [Patent Document 10] U.S. Patent Application Publication No. 2015 / 0166890 [Patent Document 11] U.S. Patent Application Publication No. 2015 / 0252265 [Non-patent literature]

[0030] [Non-Patent Document 1] SHJung et al., Jpn.J.Appl.Phys., Vol. 43, No. 3, 2004, p. 1028 [Non-Patent Document 2] SHLee et al., Appl. Phys. Lett. Vol. 73 (No. 20), 1998, pp. 2882-2883 [Non-Patent Document 3] SHLee et al., Liquid Crystals, Vol. 39 (No. 9), 2012, pp. 1141-1148. [Non-Patent Document 4] T.-J-Chen et al., Jpn.J.Appl.Phys. vol. 45, 2006, pp. 2702-2704 [Non-Patent Document 5] SHKim, L.-C-Chien, Jpn.J.Appl.Phys.43, 2004, pp. 7643-7647 [Non-Patent Document 6] Appl.Phys.Lett.1999, Volume 75 (No. 21), Page 3264 [Non-Patent Document 7] Optics Express 2004, Volume 12 (No. 7), Page 1221 [Overview of the project] [Problems that the invention aims to solve]

[0031] The present invention aims to provide a novel and suitable material for a liquid crystal medium (LC) that may contain a reactive mesogen (RM) for use in a display, which has no or reduced degree of the above-mentioned drawbacks. In particular, there is still a need for highly reliable liquid crystal media in this art. Furthermore, an object of the present invention is to provide alternative media in addition to existing media known to those skilled in the art, in order to broaden the range of available materials that enable more specific optimization of particular displays. [Means for solving the problem]

[0032] These objectives were achieved by the present invention using the materials and methods described herein. Particularly surprising, it was found that the advantageous effects described above could be obtained by using the liquid crystal host described below. [Modes for carrying out the invention]

[0033] The present invention One or more compounds of formula I, and one or more compounds selected from the group of compounds of formula IIA, IIB, IIC, and IID, However, mixtures X-1 and X-2 having the following compositions are excluded. Regarding liquid crystal media.

[0034] [ka]

[0035] During the ceremony, R L This represents a linear or branched alkyl or alkoxy group having H and 1 to 15 C atoms, wherein one or more CH2 groups in these groups are arranged such that the O atoms are not directly bonded to each other. [ka] -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, or -O-CO- may be substituted, provided that one or more H atoms are also substituted with halogens. X L R represents F, Cl, CN, CHF2, CF3, OCF3, or is the same or different from R. L It has one of the meanings, Y L represents H, F, Cl, or CH3.

[0036] [ka]

[0037] In the formula, R 2A , R 2B , R 2C and R 2D each independently represents H, an alkyl or alkenyl group having up to 15 C atoms, which group is unsubstituted, monosubstituted with CN or CF3, or at least monosubstituted with halogen, provided that in addition, in these groups, one or more CH2 groups are such that O atoms are not directly linked to each other, and are replaced by -O-, -S-, [Chemical formula] [[ID=1⑧]] -C≡C-, -CF2O-, -OCF2-, -CO-O- or -O-CO- may be replaced, L 1 ~L 4 each independently represents F, Cl, CF3 or CHF2, Y represents H, F, Cl, CF3, CHF2 or CH3, preferably H or CH3, particularly preferably H, Z 2 , Z 2B and Z 2D each independently represents a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, -CH=CHCH2O-, p represents 0, 1 or 2, q represents 0 or 1, the same or different in each occurrence, and v is an integer from 1 to 6.

[0038] [Table 1]

[0039] [Table 2]

[0040] Mixtures X-1 and X-2 are shown in European Patent Application No. 19199422.7, in which the acronyms used to designate the mixture components are described in Tables 1 to 3 and Table A. The acronyms are the same as those used herein and described in Tables A, B, C and D below.

[0041] The medium according to the present invention comprises one or more compounds of formula IIA, IIB, IIC, or IID, and stands out for its significantly improved reliability compared to currently known mediums that do not contain compounds of formula I. In particular, the voltage holding ratio (VHR) after UV light loading is improved.

[0042] The compound of formula I is preferably selected from the group of compounds of formula I-1, I-2, and I-3, preferably I-1 and I-2. [ka]

[0043] During the ceremony R L1 and R L2 The terms are identical or different and have the meanings given above in Formula I, each preferably representing an alkyl or alkenyl group having 1 to 7 carbon atoms or 2 to 7 carbon atoms, where the CH2 group may be replaced by cyclopropane-1,2-diyl.

[0044] In compounds of formulas IIA, IIB, and IID, Z 2 Z may have the same or different meanings. In the compound of formula IIB, Z 2 and Z 2B Z may have the same or different meanings. In compounds of formula IID, Z 2 and Z 2D These terms may have the same or different meanings.

[0045] In compounds of formulas IIA, IIB, IIC, and IID, R 2A , R 2B , R 2Cand R 2D These are alkyl groups, each preferably having 1 to 6 carbon atoms, particularly CH3, C2H5, n-C3H7, n-C4H9, and n-C5H 11 It represents.

[0046] In compounds of formulas IIA, IIB, and IID, L 1 , L 2 , L 3 and L 4 Preferably, L 1 =L 2 =F and L 3 =L 4 =F, and further L 1 =F and L 2 =Cl, L 1 =Cl and L 2 =F, L 3 =F and L 4 =Cl, L 3 =Cl and L 4 = Represents F. Z in equations IIA and IIB. 2 and Z 2B Preferably, each represents a single bond independently of the others, and further, a -C2H4-bridge.

[0047] In equation IIB, Z 2 = -C2H4- or -CH2O-, Z 2B It is preferably a single bond, or Z 2B = -C2H4- or -CH2O-, Z 2 It is preferably a single bond.

[0048] In formula IID, Z 2D It is preferably a single bond.

[0049] In compounds of formulas IIA, IIB, and IID, (O)C v H 2v+1 Preferably, OC v H 2v+1 This represents (O)C in compounds of formula IIC. v H 2v+1 Preferably, OC v H 2v+1 It represents.

[0050] In compounds of formula IIC, L 3 and L 4 Preferably, each represents F.

[0051] Preferred compounds for formulas IIA, IIB, IIC, and IID are shown below.

[0052] [ka]

[0053] [ka]

[0054] [ka]

[0055] [ka]

[0056] [ka]

[0057] [ka]

[0058] [ka]

[0059] [ka]

[0060] [ka]

[0061] [ka]

[0062] [ka]

[0063] [ka]

[0064] [ka]

[0065] In the formula, parameter a represents 1 or 2, and alkyl and alkyl * Each of the following independently represents a linear alkyl group having 1 to 6 carbon atoms, alkenyl represents a linear alkenyl group having 2 to 6 carbon atoms, and (O) represents an oxygen atom or a single bond. Alkenyl preferably represents CH2=CH-, CH2=CHCH2CH2-, CH3-CH=CH-, CH3-CH2-CH=CH-, CH3-(CH2)2-CH=CH-, CH3-(CH2)3-CH=CH-, or CH3-CH=CH-(CH2)2-.

[0066] A particularly preferred mixture according to the present invention comprises one or more compounds of the formulas IIA-2, IIA-8, IIA-10, IIA-16, II-18, IIA-40, IIA-41, IIA-42, IIA-43, IIB-2, IIB-10, IIB-16, IIC-1, IID-4, and IID-10.

[0067] The proportion of the compound of formula IIA and / or IIB in the overall mixture is preferably at least 20% by weight.

[0068] A particularly preferred medium according to the present invention contains at least one compound of formula IIC-1 in an amount preferably more than 3% by weight, more preferably more than 5% by weight, and most preferably 5 to 25% by weight. [ka]

[0069] In the formula, alkyl and alkyl * The above has the meanings shown.

[0070] In preferred embodiments, the medium according to the present invention comprises one or more compounds of formula III.

[0071] [ka]

[0072] During the ceremony, R 11 and R 12 Each of these independently represents an alkyl or alkoxy group having H and 1 to 15 C atoms, provided that in these groups, one or more CH2 groups are arranged such that the O atoms are not directly bonded to each other. [ka] -C≡C-, -CF2O-, -OCF2-, -CH=CH- may be replaced by -O-, -CO-O-, or -O-CO-, and one or more H atoms may be replaced by halogens. A 1 Each of them appeared independently of the others. a) A 1,4-cyclohexenylene or 1,4-cyclohexylene group in which one or two non-adjacent CH2 groups may be replaced by -O- or -S-, b) a 1,4-phenylene group in which one or two CH groups may be replaced by N, c) a group from the group consisting of spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, phenanthrene-2,7-diyl and fluorene-2,7-diyl represents, provided that the groups a), b) and c) may be mono- or polysubstituted by halogen atoms, n represents 0, 1 or 2, preferably 0 or 1, Z 1 in each occurrence is independently of one another, -CO-O-, -O-CO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-CH2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C- or a single bond, and L 11 and L 12 each independently of one another represents F, Cl, CF3 or CHF2, preferably H or F, most preferably F, and W represents O or S.

[0073] In a preferred embodiment of the invention the medium comprises one or more compounds of formula III-1 and / or III-2.

[0074]

Chemical formula

[0075] wherein the groups occurring have the same meaning as given above for formula III, preferably R 11 and R 12Each of these groups independently represents an alkyl, alkenyl, or alkoxy group having up to 15 C atoms, more preferably one or both of which represent an alkoxy group. L 11 and L 12 These preferably represent F.

[0076] In a preferred embodiment, the medium contains one or more compounds of formula III-1 selected from the group of compounds of formula III-1-1 to III-1-11, preferably formula III-1-6.

[0077] [ka]

[0078] [ka]

[0079] During the ceremony, Alkyl and alkyl * Each of these represents a linear alkyl group having 1 to 6 carbon atoms independently of each other, and is represented as alkenyl and alkenyl * Each of these represents a linear alkenyl group having 2 to 6 carbon atoms independently of each other, and alkoxy and alkoxy * Each represents a linear alkoxy group having 1 to 6 carbon atoms independently of each other, L 11 and L 12 Each represents either F or Cl, preferably both being F.

[0080] In a preferred embodiment, the medium contains one or more compounds of formula III-2 selected from the group of compounds of formula III-2-1 to III-2-11, preferably formula III-2-6.

[0081] [ka]

[0082]

Chem.

[0083] wherein, alkyl and alkyl * each independently represent a linear alkyl group having 1 to 6 carbon atoms, alkenyl and alkenyl * each independently represent a linear alkenyl group having 2 to 6 carbon atoms, alkoxy and alkoxy * each independently represent a linear alkoxy group having 1 to 6 carbon atoms, L 11 and L 12 each represent F or Cl, preferably both F.

[0084] In a preferred embodiment of the present invention, the medium comprises one or more compounds of formula IIIA-1 and / or formula IIIA-2.

[0085]

Chem.

[0086] wherein, L 11 and L 12 have the same meaning as given in formula III, (O) represents O or a single bond, R IIIA is alkyl or alkenyl having up to 7 carbon atoms or the group -C m H 2m+1 Cy represents, m and n are the same or different and are 0, 1, 2, 3, 4, 5 or 6, preferably 1, 2 or 3, very preferably 1, Cy may be substituted with an alkyl or alkenyl group having up to three carbon atoms, or with a halogen or CN, and represents an alicyclic group having three, four or five ring atoms, preferably representing cyclopropyl, cyclobutyl, or cyclopentyl.

[0087] The compounds of formula IIIA-1 and / or IIIA-2 are either substitutes or additions, preferably added, to the medium.

[0088] The following are highly preferred compounds of formulas IIIA-1 and IIIA-2.

[0089] [ka]

[0090] In the formula, alkoxy represents a linear alkoxy group having 1 to 6 carbon atoms.

[0091] In a preferred embodiment of the present invention, the medium comprises one or more compounds of formula III-3.

[0092] [ka]

[0093] During the ceremony, R 11 , R 12 -CH=CH-, -CF2O-, -OCF2-, -CH=CH [ka] It may be replaced with -O-, -CO-O-, or -O-CO-, and in addition, one or more H atoms may be replaced with halogens.

[0094] The compound of formula III-3 is preferably selected from the group of compounds of formulae III-3-1 to III-3-10.

[0095]

Chemical formula

[0096]

Chemical formula

[0097] In the formula, R 12 represents an alkyl group having 1 to 7 C atoms, preferably ethyl, n-propyl or n-butyl, or alternatively cyclopropylmethyl, cyclobutylmethyl or cyclopentylmethyl. [[ID=Z7]]

[0098] In a preferred embodiment of the present invention, the medium contains one or more compounds of formulae III-4 to III-6, preferably of formula III-5.

[0099]

Chemical formula

[0100] In the formula, the parameters have the meanings given above, and R 11 preferably represents a linear alkyl group having 1 to 7 C atoms, and R 12 preferably represents an alkoxy group having 1 to 7 C atoms.

[0101] In a preferred embodiment, the medium contains one or more compounds selected from the group of compounds of formulae III-7 to III-9, preferably of formula III-8.

[0102]

Chemical formula

[0103] In the formula, the parameter has the meaning given above, R 11 R preferably represents a linear alkyl group having 1 to 7 C atoms, 12 preferably represents an alkoxy group having 1 to 7 carbon atoms.

[0104] In preferred embodiments, the medium comprises one or more compounds of formula IV.

[0105] [ka]

[0106] During the ceremony, R 41 This represents an unsubstituted alkyl group having 1 to 7 carbon atoms or an unsubstituted alkenyl group having 2 to 7 carbon atoms, preferably an n-alkyl group (particularly preferably having 2, 3, 4, or 5 carbon atoms), and R 42 This represents an unsubstituted alkyl group having 1 to 7 carbon atoms or an unsubstituted alkoxy group having 1 to 6 carbon atoms (preferably both having 2 to 5 carbon atoms), an unsubstituted alkenyl group having 2 to 7 carbon atoms (preferably having 2, 3, or 4 carbon atoms), more preferably a vinyl group or a 1-propenyl group, particularly a vinyl group.

[0107] The compound of formula IV is preferably selected from the group of compounds of formula IV-1 to IV-4.

[0108] [ka]

[0109] During the ceremony, Alkyl and alkyl' independently represent alkyl groups having 1 to 7 carbon atoms, preferably 2 to 5 carbon atoms. Alkenyl represents an alkenyl group having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably 2 carbon atoms. 'alkenyl' represents an alkenyl group having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably 2 to 3 carbon atoms, and The term "alkoxy" represents an alkoxy having 1 to 5 carbon atoms, preferably 2 to 4 carbon atoms.

[0110] Preferably, the medium contains one or more compounds selected from the compounds of formulas IV-1-1 to IV-1-4.

[0111] [ka]

[0112] More preferably, the medium comprises one or more compounds of formula IV-2-1 and / or IV-2-2.

[0113] [ka]

[0114] More preferably, the medium according to the present invention comprises a compound of formula IV-3, preferably selected from compounds of formula IV-3-1 to IV-3-5.

[0115] [ka]

[0116] More preferably, the medium according to the present invention comprises a compound of formula IV-4, selected particularly from compounds of formula IV-4-1 and IV-4-2.

[0117] [ka]

[0118] The liquid crystal medium preferably additionally contains one or more compounds of formula IVa.

[0119]

Chemical formula

[0120] In the formula, R 41 and R 42 each independently represent a linear alkyl, alkoxy, alkenyl, alkoxyalkyl or alkoxy group having up to 12 carbon atoms.

Chemical formula

[0121] Preferred compounds of formula IVa are shown below.

[0122]

Chemical formula

[0123] In the formula, alkyl and alkyl * each independently represent a linear alkyl group having 1 to 6 carbon atoms.

[0124] The medium according to the invention preferably contains at least one compound of formula IVa-1 and / or formula IVa-2.

[0125] The proportion of the compound of formula IVa in the total mixture is preferably at least 5% by weight.

[0126] Preferably, the medium contains one or more compounds of formulae IVb-1 to IVb-3.

[0127] [ka]

[0128] During the ceremony, Alkyl and alkyl * Each represents a linear alkyl group having 1 to 6 C atoms independently of each other, and alkenyl and alkenyl * Each of these represents a linear alkenyl group having 2 to 6 carbon atoms independently of each other.

[0129] The proportion of biphenyls of formulas IVb-1 to IVb-3 in the overall mixture is preferably at least 3% by weight, and more preferably 5% by weight or more.

[0130] Among the compounds of formulas IVb-1 to IVb-3, the compound of formula IVb-2 is particularly preferred.

[0131] The biphenyls that are particularly preferred are listed below.

[0132] [ka]

[0133] In the formula, alkyl * represents an alkyl group having 1 to 6 C atoms, preferably representing n-propyl. The medium according to the present invention particularly preferably comprises one or more compounds of formula IVb-1-1 and / or IVb-2-3.

[0134] In a preferred embodiment, the medium comprises one or more compounds of formula V.

[0135] [ka]

[0136] During the ceremony, R 51 and R 52 R is independent of each other41 and R 42 It has one of the meanings given to it, and preferably represents an alkyl having 1 to 7 carbon atoms, preferably an n-alkyl, particularly preferably an n-alkyl having 1 to 5 carbon atoms, an alkoxy having 1 to 7 carbon atoms, preferably an n-alkoxy, particularly preferably an n-alkoxy having 2 to 5 carbon atoms, an alkoxyalkyl having 2 to 7 carbon atoms, preferably an alkoxyalkyl having 2 to 4 carbon atoms, an alkenyl or alkenyloxy, preferably an alkenyloxy. [ka] This represents, however, [ka] This represents, Z 51 , Z 52 Each of these independently represents -CH2-CH2-, -CH2-O-, -CH=CH-, -C≡C-, -COO- or a single bond, preferably -CH2-CH2-, -CH2-O- or a single bond, particularly preferably a single bond, and n is either 1 or 2.

[0137] The compound of formula V is preferably selected from the compounds of formulas V-1 to V-16.

[0138] [ka]

[0139] [ka]

[0140] During the ceremony, R 1 and R 2 R 2A It has the meaning shown in R. 1 and R 2Preferably, each represents a linear alkyl or alkenyl molecule independently of the others.

[0141] A preferred medium comprises one or more compounds of formulas V-1, V-3, V-4, V-6, V-7, V-10, V-11, V-12, V-14, V-15 and / or V-16.

[0142] The mixture according to the present invention is very preferably particularly containing a compound of formula V-10, V-12, V-16 and / or IV-1 in an amount of 5 to 30%.

[0143] Preferred compounds for formula V-10 are shown below.

[0144] [ka]

[0145] The medium according to the present invention particularly preferably contains a compound of formula V-10a and / or formula V-10c in combination with one or more compounds of formula IV-1. The total proportion of the compound of formula V-10a and / or formula V-10c in combination with one or more compounds selected from the compounds of formula IV-1 is 5 to 40%, and very particularly preferably 15 to 35%.

[0146] A particularly preferred mixture comprises compounds V-10a and IV-1-3 and / or IV-1-4.

[0147] [ka]

[0148] Compounds V-10a and IV-1-3 and / or IV-1-4 are preferably present in the mixture at a concentration of 15-35%, particularly preferably 15-25%, and especially preferably 18-22% relative to the total mixture.

[0149] A particularly preferred mixture comprises compounds V-10b and IV-1-3 and / or IV-1-4.

[0150] [ka]

[0151] Compounds V-10b and IV-1-3 and / or IV-1-4 are preferably present in the mixture at a concentration of 15-35%, particularly preferably 15-25%, and especially preferably 18-22% relative to the total mixture.

[0152] A particularly preferred mixture contains the following three compounds:

[0153] [ka]

[0154] Compounds V-10a, V-10b, and IV-1-1 are preferably present in the mixture at a concentration of 15-35%, particularly preferably 15-25%, and especially preferably 18-22% of the total mixture.

[0155] A preferred mixture contains at least one compound selected from the group of compounds listed below.

[0156] [ka]

[0157] In the formula, R 41 and R 42 , and R 51 and R 52 The above has the meaning. Preferably, in compounds V-6, V-7 and IV-1, R 41 and R 51 R represents an alkyl or alkenyl having 1 to 6 or 2 to 6 C atoms, 42 and R 52This represents an alkenyl having 2 to 6 carbon atoms.

[0158] Preferred media include at least one compound of formulas V-6a, V-6b, V-7a, V-7b, IV-4-1, IV-4-2, IV-3a, and IV-3b.

[0159] [ka]

[0160] In the formula, alkyl represents an alkyl group having 1 to 6 carbon atoms, and alkenyl represents an alkenyl group having 2 to 6 carbon atoms.

[0161] The compounds of formulas V-6a, V-6b, V-7a, V-7b, IV-4-1, IV-4-2, IV-3a, and IV-3b are preferably present in the mixture according to the present invention in an amount of 1 to 40% by weight, preferably 5 to 35% by weight, and very preferably 10 to 30% by weight.

[0162] In a preferred embodiment of the present invention, the medium further comprises one or more compounds of formulas VI-1 to VI-9.

[0163] [ka]

[0164] [ka]

[0165] During the ceremony, R 7 Each of them independently of the other in claim 5 is R 2A It has one of the meanings shown in, and w and x each represent 1 through 6 independently of each other.

[0166] A mixture containing at least one compound of formula V-9 is particularly preferred.

[0167] In a preferred embodiment of the present invention, the medium further comprises one or more compounds of formulas VII-1 to VII-21.

[0168] [ka]

[0169] [ka]

[0170] [ka]

[0171] During the ceremony R represents a linear alkyl or alkoxy group having 1 to 6 carbon atoms, (O) represents -O- or a single bond, m is 0, 1, 2, 3, 4, 5, or 6, and n is 0, 1, 2, 3, or 4.

[0172] R preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, or pentoxy.

[0173] The medium according to the present invention preferably contains 2 to 30% by weight, particularly 5 to 20% by weight, of terphenyls of formulas VII-1 to VII-21.

[0174] Compounds of formulas VII-1, VII-2, VII-4, VII-20, and VII-21 are particularly preferred. In these compounds, R preferably represents an alkyl group having 1 to 5 carbon atoms, and more preferably an alkoxy group. In the compound of formula VII-20, R preferably represents an alkyl or alkenyl group, particularly an alkyl group. In the compound of formula VII-21, R preferably represents an alkyl group.

[0175] When the Δn value of the mixture is 0.1 or higher, terphenyl compounds are preferably used in the mixture according to the present invention. The preferred mixture contains one or more terphenyl compounds selected from the group of compounds VII-1 to VII-21 in an amount of 2 to 20% by weight.

[0176] Further preferred embodiments are listed below.

[0177] a) A liquid crystal medium containing at least one compound of formulas Z-1 to Z-7.

[0178] [ka]

[0179] In the formula, R and alkyl have the meanings shown in Formula III above.

[0180] b) A preferred liquid crystal medium according to the present invention comprises one or more substances containing tetrahydronaphthyl or naphthyl units, such as compounds of formula N-1 to N-5.

[0181] [ka]

[0182] R in the formula 1N and R 2N Each of them is R independently of the others. 2A It has the meaning shown in, preferably representing a linear alkyl, linear alkoxy or linear alkenyl, and Z 1 and Z 2 These each independently represent -C2H4-, -CH=CH-, -(CH2)4-, -(CH2)3O-, -O(CH2)3-, -CH=CHCH2CH2-, -CH2CH2CH=CH-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, -CF=CH-, -CH=CF-, -CF2O-, -OCF2-, -CH2-, or a single bond.

[0183] c) A preferred mixture comprises one or more compounds selected from the group consisting of difluorodibenzochromane compounds of formula BC, chromanes of formula CR, and fluorinated phenanthrenes of formulas PH-1 and PH-2.

[0184] [ka]

[0185] During the ceremony R B1 , R B2 , R CR1 , R CR2 , R 1 , R 2 Each of them is R independently of the others. 2A It has the meaning of c being 0, 1, or 2. 1 and R 2 Preferably, each represents an alkyl or alkoxy having 1 to 6 C atoms independently of each other.

[0186] The mixture according to the present invention preferably contains compounds of formulas BC, CR, PH-1, and PH-2 in an amount of 3 to 20% by weight, and particularly in an amount of 3 to 15% by weight.

[0187] Particularly preferred compounds of formulas BC and CR are compounds BC-1 to BC-7 and CR-1 to CR-5.

[0188] [ka]

[0189] [ka]

[0190] During the ceremony, Alkyl and alkyl * Each of these independently represents a linear alkyl group having 1 to 6 carbon atoms. alkenyl and alkenyl * Each of these independently represents a linear alkenyl group having 2 to 6 carbon atoms.

[0191] A mixture containing one, two, or three compounds of formula BC-2, BF-1, and / or BF-2 is very preferably preferred.

[0192] d) A preferred mixture comprises one or more indane compounds of formula In.

[0193] [ka]

[0194] During the ceremony, R 11 , R 12 , R 13 Each of these represents a linear alkyl, alkoxy, alkoxyalkyl, or alkenyl group having 1 to 6 carbon atoms independently of each other. R 12 and R 13 This is represented by adding a halogen, preferably F, [ka] i represents 0, 1, or 2.

[0195] Preferred compounds of formula In are the compounds of formula In-1 to In-16 shown below.

[0196] [ka]

[0197] [ka]

[0198] Compounds of formulas In-1, In-2, In-3, and In-4 are particularly preferred.

[0199] Compounds of formula In and sub-formulas In-1 to In-16 are preferably used in the mixture according to the present invention at a concentration of 5% by weight or more, particularly 5 to 30% by weight, and very preferably 5 to 25% by weight.

[0200] e) A preferred mixture contains one or more compounds of formulas L-1 to L-5.

[0201] [ka]

[0202] During the ceremony R and R 2 Each of them independently of the other in equation IIA above is R 2A The meaning shown is as follows: alkyl represents an alkyl group having 1 to 6 carbon atoms. The parameter s represents 1 or 2.

[0203] The compounds of formulas L-1 to L-5 are preferably used at a concentration of 5 to 50% by weight, particularly 5 to 40% by weight, and very preferably 10 to 40% by weight.

[0204] f) A preferred mixture includes one or more compounds of formula IIA-Y in addition.

[0205] [ka]

[0206] In the formula, R 11 and R 12 In equation IIA above, R 2A It has one of the meanings shown, L 1 and L 2 These represent F or Cl, either identical or different.

[0207] The preferred compounds of formula IIA-Y are selected from the group consisting of the following sub-formulas.

[0208] [ka]

[0209] [ka]

[0210] In the formula, Alkyl and Alkyl * Each of these independently represents a linear alkyl group having 1 to 6 carbon atoms, Alkoxy represents a linear alkoxy group having 1 to 6 carbon atoms, and Alkenyl and Alkenyl * Each represents a linear alkenyl group having 2 to 6 C atoms independently of each other, and O represents an oxygen atom or a single bond. * Preferably, CH2=CH-, CH2=CHCH2CH2-, CH3-CH=CH-, CH3-CH2-CH=CH-, CH3-(CH2)2-CH=CH-, CH3-(CH2)3-CH=CH-, or CH3-CH=CH-(CH2)2-.

[0211] Particularly preferred compounds of formula IIA-Y are selected from the group consisting of the following sub-formulas.

[0212] [ka]

[0213] In the formula, Alkoxy and Alkoxy * The terms have the meanings defined above, and preferably represent methoxy, ethoxy, n-propyloxy, n-butyloxy, or n-pentyloxy.

[0214] The liquid crystal medium according to the present invention, also referred to herein as a liquid crystal host mixture, is suitable for use in polymer-stabilized displays. For this purpose, the medium according to the present invention may contain one or more polymerizable compounds of formula P.

[0215] [ka]

[0216] In the formula, each base, independently of the others, has the following meanings, whether identical or different in each instance: P is a polymerizable group, Sp is a spacer group or a single bond. A 1 , A 2 Preferably, the group is an aromatic, heteroaromatic, alicyclic, or heterocyclic group having 4 to 25 ring atoms, and the group may include a fused ring, and the group is unsubstituted or monosubstituted or polysubstituted with L. Z 1 -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -(CH2) n1 -, -CF2CH2-, -CH2CF2-, -(CF2) n1 -, -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH-, -CH2-CH2-CO-O-, -O-CO-CH2-CH2-, -CR 0 R 00 -or single bond, R 0 , R 00 It is an alkyl having H or 1 to 12 C atoms, R is H, L, or P-Sp-, L is a linear, branched, or cyclic alkyl group having F, Cl, -CN, P-Sp-, or 1 to 25 C atoms, wherein one or more non-adjacent CH2 groups may be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- such that the O and / or S atoms are not directly linked to each other, and one or more H atoms may be replaced with P-Sp-, F, or Cl. z is 0, 1, 2, or 3. n1 is 1, 2, 3, or 4.

[0217] As used herein, the terms “active layer” and “switchable layer” refer to layers in electro-optical displays, such as LC displays, that contain one or more molecules having structural and optical anisotropy, such as LC molecules, whose orientation changes in response to external stimuli, such as electric or magnetic fields, resulting in a change in the transparency of the layer to polarized or unpolarized light.

[0218] As used herein, the terms “tilt” and “tilt angle” mean the tilted orientation of LC molecules in an LC medium relative to the cell surface in an LC display (preferably a PSA display). In this specification, the tilt angle means the average angle (less than 90°) between the molecular long axis (LC director) of the LC molecule and the surface of the flat, parallel outer plate forming the LC cell. In this specification, a low tilt angle (i.e., far from 90°) corresponds to a large tilt. Appropriate methods for measuring the tilt angle are given in the examples. Unless otherwise indicated, the tilt angle values ​​disclosed above and below refer to this measurement method.

[0219] As used herein, the terms “reactive mesogen” and “RM (reactive mesogen)” are understood to mean a compound containing a mesogen or liquid crystal skeleton and one or more functional groups linked to that skeleton and suitable for polymerization, and the functional group is also referred to as a “polymerizable group” or “P”.

[0220] Unless otherwise specified, the term "polymerizable compound" in this specification shall be understood to mean a polymerizable monomer compound.

[0221] As used herein, the term "low molecular weight compound" is understood to mean a monomer and / or a compound not prepared by polymerization, as opposed to "polymer compound" or "polymer."

[0222] As used herein, the term "non-polymerizable compound" means a compound that does not contain functional groups suitable for polymerization under the conditions normally applied for the polymerization of RM.

[0223] As used herein, the term “mesogenic group” refers to a group known to those skilled in the art and documented in the literature, which, due to the anisotropy of its attractive and repulsive interactions, essentially contributes to the formation of a liquid-crystalline (LC) phase in low-molecular-weight or high-molecular-weight materials. Compounds containing mesogenic groups (mesogenic compounds) do not necessarily have an LC phase themselves. It is also possible for mesogenic compounds to exhibit LC phase behavior only after mixing with other compounds and / or polymerization. Typical mesogenic groups are, for example, rigid rod-shaped or disc-shaped units. An overview of the terms and definitions used with respect to mesogenic or LC compounds is given in Pure Appl. Chem. 2001, Vol. 73 (No. 5), p. 888 and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, Vol. 116, pp. 6340–6368.

[0224] As used herein, the terms “optically active” and “chiral” are synonymous with materials that can induce a helical pitch in a nematic host material, and are also referred to as “chiral dopant.”

[0225] As used herein, the term “spacer group” is also hereafter referred to as “Sp,” and is known to those skilled in the art and described in the literature, see, for example, Pure Appl. Chem. 2001, Vol. 73 (No. 5), p. 888 and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, Vol. 116, pp. 6340–6368. As used herein, the term “spacer group” or “spacer” means a flexible group, such as an alkylene group, that links a mesogenic group and one or more polymerizable groups in a polymerizable mesogenic compound.

[0226] Above and below, [ka] This represents a trans-1,4-cyclohexylene ring.

[0227] base [ka] In this example, the single bond between the two ring atoms can be linked to any unbonded position on the benzene ring.

[0228] In the above and below, "organic group" refers to a carbon or hydrocarbon group.

[0229] The term "carbon group" refers to a monovalent or polyvalent organic group containing at least one carbon atom, which may either contain no further atoms (e.g., -C≡C-) or may contain one or more further atoms (e.g., carbonyl), such as N, O, S, B, P, Si, Se, As, Te, or Ge. The term "hydrocarbon group" refers to a carbon group that additionally contains one or more H atoms and may contain one or more heteroatoms, such as N, O, S, B, P, Si, Se, As, Te, or Ge.

[0230] "Halogen" represents F, Cl, Br, or I, preferably F or Cl.

[0231] -CO-, -C(=O)-, and -C(O)- are carbonyl groups, i.e., [ka] It represents.

[0232] The carbon or hydrocarbon group may be either saturated or unsaturated. Unsaturated groups include, for example, aryl, alkenyl, or alkynyl groups. Carbon or hydrocarbon groups having more than three C atoms may be linear, branched, and / or cyclic, and may also contain spirolinks or fused rings.

[0233] Furthermore, terms such as "alkyl," "aryl," and "heteroaryl" also encompass polyvalent groups, such as alkylenes, arylenes, and heteroarylenes.

[0234] The term "aryl" refers to an aromatic carbon group or a group derived therefrom. The term "heteroaryl" refers to an "aryl" as defined above, containing one or more heteroatoms (preferably selected from N, O, S, Se, Te, Si, and Ge).

[0235] Preferred carbon and hydrocarbon groups are linear, branched, or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy and alkoxycarbonyloxy groups having 1 to 40, preferably 1 to 20, and particularly preferably 1 to 12 carbon atoms, which may be substituted; aryl or aryloxy groups having 5 to 30, preferably 6 to 25 carbon atoms, which may be substituted; or alkylaryl, arylalkyl, alkylaryloxy, arylalkyloxy, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy and aryloxycarbonyloxy groups having 5 to 30, preferably 6 to 25 carbon atoms, wherein one or more carbon atoms may be replaced by heteroatoms selected from N, O, S, Se, Te, Si, and Ge.

[0236] Further preferred carbon and hydrocarbon groups are C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkinyl, C3~C 20 Allyl, C4~C 20 Alkyldienyl, C4~C 20 Polyenyl, C6~C 20 Cycloalkyl, C4~C 15 Cycloalkenyl, C6~C 30 Aryl, C6~C 30 Alkylaryl, C6~C30 Arylalkyl, C6~C 30 Alkylaryloxy, C6~C 30 Arylalkyloxy, C2~C 30 Heteroaryl, C2~C 30 It is a heteroaryloxy.

[0237] C1~C 12 Alkyl, C2~C 12 Alkenyl, C2~C 12 Alkinyl, C6~C 25 Aryl and C2~C 25 Heteroaryls are particularly preferred.

[0238] Further preferred carbon and hydrocarbon groups are linear, branched, or cyclic alkyl groups having 1 to 20, preferably 1 to 12 C atoms, the group being unsubstituted or monosubstituted or polysubstituted with F, Cl, Br, I, or CN, wherein one or more non-adjacent CH2 groups are independently linked to each other such that the O and / or S atoms are not directly linked to one another, and each is -C(R x )=C(R x )-, -C≡C-, -N(R x )-, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- should be replaced with these.

[0239] R x Preferably, represents H, F, Cl, CN, a linear, branched, or cyclic alkyl chain having 1 to 25 carbon atoms (wherein one or more non-adjacent carbon atoms may be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, and one or more H atoms may be replaced by F or Cl), or an aryl or aryloxy group having 6 to 30 carbon atoms, which may be substituted, or a heteroaryl or heteroaryloxy group having 2 to 30 carbon atoms, which may be substituted.

[0240] Preferred alkyl groups include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, n-hexyl, cyclohexyl, 2-ethylhexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, dodecanyl, trifluoromethyl, perfluoro-n-butyl, 2,2,2-trifluoroethyl, perfluorooctyl, and perfluorohexyl.

[0241] Preferred alkenyl groups include, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, and cyclooctenyl.

[0242] Preferred alkynyl groups include, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, and octinyl.

[0243] Preferred alkoxy groups include, for example, methoxy, ethoxy, 2-methoxyethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, 2-methylbutoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy, n-nonoxy, n-decoxy, n-undecoxy, and n-dodecoxy.

[0244] Preferred amino groups include, for example, dimethylamino, methylamino, methylphenylamino, and phenylamino.

[0245] The aryl and heteroaryl groups may be monocyclic or polycyclic; that is, they may contain one ring (e.g., phenyl) or two or more rings, and the group may be condensed (e.g., naphthyl) or covalently linked (e.g., biphenyl), or may contain a combination of condensed and linked rings. The heteroaryl group preferably contains one or more heteroatoms selected from O, N, S, and Se.

[0246] Monocyclic, bicyclic, or tricyclic aryl groups having 6 to 25 carbon atoms and monocyclic, bicyclic, or tricyclic heteroaryl groups having 5 to 25 ring atoms are particularly preferred, and these groups may contain fused rings or be substituted. Furthermore, 5-membered, 6-membered, or 7-membered aryl and heteroaryl groups are preferred, however, one or more CH groups may be replaced with N, S, or O such that the O atoms and / or S atoms are not directly linked to each other.

[0247] Preferred aryl groups include, for example, phenyl, biphenyl, terphenyl, [1,1':3',1”]terphenyl-2'-yl, naphthyl, anthracene, binaphthyl, phenanthrene, 9,10-dihydrophenanthrene, pyrene, dihydropyrene, chrysene, perylene, tetracene, pentacene, benzopyrene, fluorene, indene, indenofluorene, and spirobifluorene.

[0248] Preferred heteroaryl groups include, for example, pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, furan, thiophene, selenofen, oxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4- Five-membered rings such as thiadiazole, 1,2,5-thiadiazole, and 1,3,4-thiadiazole; six-membered rings such as pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, and 1,2,3,5-tetrazine; or indole, isoindole, indidine, indazole, benzimidazole, benzotriazole, pli Naphthymidazole, phenanthroidazole, pyridymidazole, pyrazineimidazole, quinoxalineimidazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, benzothiazole, benzofuran, isobenzofuran, dibenzofuran, quinoline, isoquinoline, pteridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, benzo- Condensation groups such as soquinoline, acridine, phenothiazine, phenoxazine, benzopyridazine, benzopyrimidine, quinoxaline, phenazine, naphthyridine, azacarbazole, benzocarbolin, phenantholidine, phenanthroline, thieno[2,3b]thiophene, thieno[3,2b]thiophene, dithienothiophene, isobenzothiophene, dibenzothiophene, benzothiadiazothiophene; or combinations thereof.

[0249] Furthermore, the aryl and heteroaryl groups described above and below may be substituted with alkyl, alkoxy, thioalkyl, fluorine, fluoroalkyl, or further aryl or heteroaryl groups.

[0250] (Non-aromatic) alicyclic and heterocyclic groups include both saturated rings, i.e., those containing exclusively single bonds, and partially unsaturated rings, i.e., those which may also contain multiple bonds. Heterocyclic rings preferably contain one or more heteroatoms selected from Si, O, N, S, and Se.

[0251] (Non-aromatic) alicyclic and heterocyclic groups may be monocyclic, i.e., containing only one ring (e.g., cyclohexane), or polycyclic, i.e., containing multiple rings (e.g., decahydronaphthalene or bicyclooctane). Saturated groups are particularly preferred. Furthermore, monocyclic, bicyclic, or tricyclic groups having 5 to 25 ring atoms are preferred, and these groups may contain fused rings or be substituted. Furthermore, 5-membered, 6-membered, 7-membered, or 8-membered carbocyclic groups are preferred, provided that one or more C atoms are replaced by Si, and / or one or more CH groups are replaced by N, and / or one or more non-adjacent CH2 groups are replaced by -O- and / or -S-.

[0252] Preferred alicyclic and heterocyclic groups include, for example, five-membered groups such as cyclopentane, tetrahydrofuran, tetrahydrothiofuran, and pyrrolidine; six-membered groups such as cyclohexane, silinane, cyclohexene, tetrahydropyran, tetrahydrothiopyran, 1,3-dioxane, 1,3-dithiane, and piperidine; seven-membered groups such as cycloheptane; and condensation groups such as tetrahydronaphthalene, decahydronaphthalene, indane, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, and octahydro-4,7-methanoindan-2,5-diyl.

[0253] Preferred substituents include, for example, dissolution-promoting groups such as alkyl or alkoxy groups, electron-withdrawing groups such as fluorine, nitro or nitrile groups, or substituents that increase the glass transition temperature (Tg) in the polymer, particularly bulky groups such as t-butyl or optionally substituted aryl groups.

[0254] Preferred substituents are referred to as "L" below. S It is also called, for example, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, -C(=O)N(R x )2, -C(=O)Y 1 -C(=O)R x , -N(R x )2. A linear or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms each (wherein one or more H atoms may be replaced with F or Cl), a silyl having 1 to 20 Si atoms which may be substituted, or an aryl having 6 to 25, preferably 6 to 15 C atoms which may be substituted.

[0255] In the formula, R x represents an alkyl chain having 1 to 25 carbon atoms, wherein one or more non-adjacent CH2 groups may be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, such that the O- and / S- atoms are not directly linked to each other, wherein one or more H atoms may be replaced with F, Cl, P- or P-Sp-, and Y 1 This represents halogen.

[0256] "Substituted silyl or aryl" is preferably a halogen, -CN, R 0 , -OR 0 ,-CO-R 0 , -CO-OR 0 ,-O-CO-R 0 or -O-CO-OR 0This means substitution by R, however, 0 represents an alkyl group having H or 1 to 20 C atoms.

[0257] Particularly preferred substituents L include, for example, F, Cl, CN, NO2, CH3, C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5, and phenyl.

[0258] A 1 and A 2 Very preferably [ka] This represents, where L has one of the meanings shown above, and r represents 0, 1, 2, 3 or 4, in particular [ka] That is the case.

[0259] The polymerizable group P is suitable for polymerization reactions such as free radical or ionic chain polymerization, polyaddition or polycondensation, or for polymer-like reactions such as addition or condensation onto a polymer backbone. Groups for chain polymerization, particularly those containing a C=C double bond or a C≡C triple bond, and groups suitable for ring-opening polymerization, such as oxetane or epoxide groups, are especially preferred.

[0260] The preferred group P is CH2=CW 1 -CO-O-, CH2=CW 1 -CO-, [ka] CH2=CW 2 -(O) k3 -, CW 1 =CH-CO-(O) k3 -, CW 1 =CH-CO-NH-, CH2=CW 1-CO-NH-, CH3-CH=CH-O-, (CH2=CH)2CH-OCO-, (CH2=CH-CH2)2CH-OCO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, HO-CW 2 W 3 -, HS-CW 2 W 3 -, HW 2 N-, HO-CW 2 W 3 -NH-, CH2=CW 1 -CO-NH-, CH2=CH-(COO) k1 -Phe-(O) k2 -, CH2=CH-(CO) k1 -Phe-(O) k2 -, Phe-CH=CH-, HOOC-, OCN- and W 4 W 5 W 6 Selected from the group consisting of Si-, in the formula, W 1 This represents H, F, Cl, CN, CF3, phenyl, or alkyl having 1 to 5 C atoms, in particular H, F, Cl or CH3, and W 2 and W 3 Each of these independently represents an alkyl group having H or 1 to 5 C atoms, particularly H, methyl, ethyl, or n-propyl, and W 4 , W 5 and W 6 Each of these independently represents Cl, an oxaalkyl or oxacarbonylalkyl having 1 to 5 C atoms, and W 7 and W 8 k1, k2, and k3 each independently represent H, Cl, or an alkyl group having 1 to 5 C atoms; Phe represents 1,4-phenylene which may be substituted with one or more groups L as defined above, other than P-Sp-; k1, k2, and k3 each independently represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.

[0261] A very preferred group P is CH2=CW 1 -CO-O-, CH2=CW 1 -CO-, [ka] CH2=CW 2 -O-, CH2=CW 2 -, CW 1 =CH-CO-(O) k3 -, CW 1 =CH-CO-NH-, CH2=CW 1 -CO-NH-, (CH2=CH)2CH-OCO-, (CH2=CH-CH2)2CH-OCO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, CH2=CW 1 -CO-NH-, CH2=CH-(COO) k1 -Phe-(O) k2 -, CH2=CH-(CO) k1 -Phe-(O) k2 -, Phe-CH=CH- and W 4 W 5 W 6 Selected from the group consisting of Si-, in the formula, W 1 This represents H, F, Cl, CN, CF3, phenyl, or alkyl having 1 to 5 C atoms, in particular H, F, Cl or CH3, and W 2 and W 3 Each of these independently represents an alkyl group having H or 1 to 5 C atoms, particularly H, methyl, ethyl, or n-propyl, and W 4 , W 5 and W 6 Each of these independently represents Cl, an oxaalkyl or oxacarbonylalkyl having 1 to 5 C atoms, and W 7 and W 8 k1, k2, and k3 each independently represent H, Cl, or an alkyl group having 1 to 5 C atoms, Phe represents 1,4-phenylene, k1, k2, and k3 each independently represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.

[0262] A particularly preferred group P is CH2=CW 1-CO-O-, in particular CH2=CH-CO-O-, CH2=C(CH3)-CO-O- and CH2=CF-CO-O-, furthermore CH2=CH-O-, (CH2=CH)2CH-O-CO-, (CH2=CH)2CH-O-, [ka] Select from the group consisting of [the specified characters].

[0263] A more preferred polymerizable group P is selected from the group consisting of vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane, and epoxide groups, and most preferably selected from acrylate and methacrylate.

[0264] When the spacer group Sp is different from the single bond, Sp is preferably of the formula Sp"-X", where Sp" and X" have the following meanings, such that each group P-Sp- corresponds to the formula R-Sp"-X"-.

[0265] Sp'' represents a linear or branched alkylene having 1 to 20, preferably 1 to 12, carbon atoms, the group may be monosubstituted or polysubstituted with F, Cl, Br, I, or CN, except that one or more non-adjacent CH2 groups are independently -O-, -S-, -NH-, -N(R) such that the O and / or S atoms are not directly linked to each other. 0 )-,-Si(R 0 R 00 )-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -S-CO-, -CO-S-, -N(R 00 )-CO-O-,-O-CO-N(R 0 )-,-N(R 0 )-CO-N(R 00 )-, -CH=CH- or -C≡C- may also be used as substitutes. “X” is -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CO-N(R 0 )-,-N(R 0 )-CO-, -N(R 0)-CO-N(R 00 )-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CR 0 -, -CY 2 =CY 3 -, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH-, or single bond are represented. R 0 and R 00 Each of these independently represents an alkyl group having either H or 1 to 20 C atoms. Y 2 and Y 3 Each of these elements independently represents either H, F, Cl, or CN.

[0266] X" is sometimes -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR 0 -, -NR 0 -CO-, -NR 0 -CO-NR 00 -or it is a single bond.

[0267] Typical spacer bases Sp and -Sp”-X”- are, for example, -(CH2) p1 -,-(CH2) p1 -O-, -(CH2) p1 -O-CO-, -(CH2) p1 -CO-O-, -(CH2) p1 -O-CO-O-, -(CH2CH2O) q1 -CH2CH2-, -CH2CH2-S-CH2CH2-, -CH2CH2-NH-CH2CH2- or -(SiR 0 R 00 -O) p1 -In the formula, p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, R 0 and R 00 The above has the meanings shown.

[0268] Particularly preferred spacer bases Sp and -Sp”-X”- are -(CH2) p1 -,-(CH2) p1 -O-, -(CH2) p1 -O-CO-, -(CH2) p1 -CO-O-, -(CH2) p1 -O-CO-O-, where p1 and q1 have the meanings shown above.

[0269] Particularly preferred groups Sp'' in their linear forms are ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylenethioethylene, ethylene-N-methyliminoethylene, 1-methylalkylene, etenylene, propenylene, and butenylene.

[0270] In a preferred embodiment of the present invention, compounds of formula P and its subformulas are such that the group Sp-P is Sp(P) s It contains a spacer group Sp (branched polymerizable group) substituted with one or more polymerizable groups P to correspond to (where s is 2 or greater).

[0271] A preferred compound of formula P according to this preferred embodiment is one in which s is 2, i.e., a compound containing the group Sp(P)2. A very preferred compound of formula P according to this preferred embodiment contains a group selected from the following formulas.

[0272] [ka]

[0273] In the formula, P is defined as in formula P, Alkyl groups represent linear or branched alkylenes having single bonds or 1 to 12 carbon atoms, and the group is either unsubstituted or monosubstituted or polysubstituted with F, Cl, or CN, provided that one or more non-adjacent CH2 groups are each independently bonded to each other such that the O and / or S atoms are not directly bonded to each other, and -C(R 0 )=C(R 0 )-, -C≡C-, -N(R 0 )-, -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- may be substituted, however R 0 It has the meaning shown above, aa and bb each independently represent 0, 1, 2, 3, 4, 5, or 6. X has one of the meanings shown in "X", and is preferably O, CO, SO2, O-CO-, CO-O, or a single bond.

[0274] The preferred spacer base Sp(P)2 is selected from formulas S1, S2, and S3.

[0275] A highly preferred spacer base Sp(P)2 is selected from the following sub-formulas.

[0276] [ka]

[0277] In the compounds of formula P and its subformulas as described above and below, P is preferably selected from the group consisting of vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane, and epoxide, most preferably from acrylate and methacrylate.

[0278] All polymerizable groups P present in the compound have the same meaning, and compounds of formula P and its subformulas as described above and below are more preferably acrylate or methacrylate, most preferably methacrylate.

[0279] In the compounds of formula P and its sub-formulas as described above and below, R preferably represents P-Sp.

[0280] Sp is a single bond or -(CH2) p1 -, -O-(CH2) p1 -, -O-CO-(CH2) p1 Or -CO-O-(CH2) p1 This represents, where p1 is 2, 3, 4, 5 or 6, and Sp is -O-(CH2) p1 -, -O-CO-(CH2) p1 or -CO-O-(CH2) p1 In this case, compounds of formula P and its sub-formulas as described above and below, in which the O atom or CO group is linked to a benzene ring, are even more preferred.

[0281] Compounds of formula P and its subformulas as described above and below, in which at least one group Sp is a single bond, are even more preferred.

[0282] At least one group Sp differs from a single bond, preferably -(CH2) p1 -, -O-(CH2) p1 -,-O-CO-(CH2) p1 or -CO-O-(CH2) p1 Selected from, where p1 is 2, 3, 4, 5 or 6, and Sp is -O-(CH2) p1 -, -O-CO-(CH2) p1 or -CO-O-(CH2) p1 In this case, compounds of formula P and its sub-formulas as described above and below, in which the O atom or CO group is linked to a benzene ring, are even more preferred.

[0283] A highly preferred base in formula P -A 1 -(ZA 2 ) z - is selected from the following formula.

[0284] [ka]

[0285] In the formula, at least one benzene ring is substituted with at least one group L, and the benzene ring may be further substituted with one or more groups L or P-Sp-.

[0286] Preferred compounds of formula P and its subformulas are selected from the following preferred embodiments (including any combination thereof): • All groups P in a compound have the same meaning. ·-A 1 -(ZA 2 ) z - is selected from A1, A2, and A5. The compound has exactly two polymerizable groups (represented by group P). The compound has exactly three polymerizable groups (represented by group P). P is selected from the group consisting of acrylate, methacrylate, and oxetane, and is very preferably acrylate or methacrylate. P is methacrylate. • All Sp groups are single bonds. • At least one of the Sp groups is a single bond, and at least one of the Sp groups is not a single bond. • If Sp is different from a single bond, -(CH2) p2 -,-(CH2) p2 -O-, -(CH2) p2 -CO-O-, -(CH2) p2 The compound is -O-CO-, where p2 is 2, 3, 4, 5, or 6, and the O atom or CO group is linked to a benzene ring. • Sp is a single bond, or -(CH2) p2 -,-(CH2) p2 -O-, -(CH2) p2 -CO-O-, -(CH2) p2 The formula represents -O-CO-, where p2 is 2, 3, 4, 5, or 6, and the O atom or CO group is linked to a benzene ring. ·R represents P-Sp- • R does not represent or does not contain a polymerizable group. • R does not represent or does not contain a polymerizable group, and represents an alkyl group having 1 to 25 C atoms in a linear, branched, or cyclic structure, wherein one or more non-adjacent CH2 groups may be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, such that the O and / or S atoms are not directly linked to each other, wherein one or more H atoms are each F, Cl, or L a It can be replaced with this. L or L' represents F, Cl, or CN. L is F.

[0287] A suitable and preferred compound for formula P is selected from the following formulas.

[0288] [ka]

[0289] [ka]

[0290] [ka]

[0291] [ka]

[0292] [ka]

[0293] [ka]

[0294] In the formula, each base has the following meaning: P 1 , P 2 and P 3 Each of these independently represents an acrylate or methacrylate group. Sp 1 , Sp 2 and Sp 3 Each represents a spacer that independently has one of the meanings indicated above and below a single bond or Sp, and is particularly preferably -(CH2) p1 -,-(CH2) p1 -O-, -(CH2) p1 -CO-O-, -(CH2) p1 -O-CO- or -(CH2) p1 -O-CO-O- represents -O-CO-O-, where p1 is an integer between 1 and 12. However, in addition, there exists base P 1 -Sp 1 -, P 2 -Sp 2 -and P 3 -Sp 3 - At least one of R aa One or more base P 1 -Sp 1 -, P 2 -Sp 2 -and P 3 -Sp 3 - is R aa It can also represent, R aa This refers to H, F, Cl, CN, or linear or branched alkyl groups having 1 to 25 C atoms (however, one or more non-adjacent CH2 groups are independently linked to each other such that the O and / or S atoms are not directly linked to each other, and each is C(R) 0 )=C(R 00 )-, -C≡C-, -N(R 0 ) may be replaced by -, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, in addition, one or more H atoms may be replaced by F, Cl, CN or P1 -Sp 1 - may be replaced by ), particularly preferably an alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, which may be linear or branched and monofluorinated or polyfluorinated (wherein alkenyl and alkynyl groups have at least 2 C atoms, and branched groups have at least 3 C atoms). R 0 , R 00 Each of these independently represents an alkyl group having H or 1 to 12 C atoms, identical or different in each occurrence. R y and R z Each of these independently represents H, F, CH3, or CF3. X 1 , X 2 and X 3 These each represent, independently of each other, -CO-O-, -O-CO-, or a single bond. Z 1 -O-, -CO-, -C(R y R z )- or -CF2CF2- represents, Z 2 and Z 3 These are, independently of each other, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-, or -(CH2) n - represents, where n is 2, 3, or 4. L, in each instance, may be the same or different, representing F, Cl, CN, or an alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, whether linear or branched and monofluorinated or polyfluorinated, preferably F. L' and L'' each represent H, F, or Cl independently of each other. k represents 0 or 1, r represents 0, 1, 2, 3, or 4. s represents 0, 1, 2, or 3. t represents 0, 1, or 2. x represents either 0 or 1.

[0295] Compounds of formulas P2, P13, P17, P22, P23, P24, P30, P31, and P32 are particularly preferred.

[0296] Furthermore, trireactive compounds P15 to P30 are preferred, particularly P17, P18, P19, P22, P23, P24, P25, P26, P30, P31, and P32.

[0297] In compounds of formulas P1 to P32, the group [ka]

[0298] However, L has one of the meanings given above and below, whether the same or different in each occurrence, preferably F, Cl, CN, NO2, CH3, C2H5, C(CH3)3, CH(CH3)2, CH2CH(CH3)C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5 or P-Sp-, very preferably F, Cl, CN, CH3, C2H5, OCH3, COCH3, OCF3 or P-Sp-, more preferably F, Cl, CH3, OCH3, COCH3 or OCF3, in particular F or CH3.

[0299] The medium according to the present invention comprises one or more chiral dopants. Preferably, these chiral dopants are 1 μm in size. -1 ~150μm -1 A range of preferably 10 μm -1 ~100μm -1The absolute value of the helical twisting power (HTP) is within the range. If the medium contains two or more chiral dopants, these may have opposite signs in their HTP values. This condition is preferable for some specific embodiments because it allows for some degree of compensation for the chirality of each compound, and can be used to compensate for various temperature-dependent properties of the medium obtained in the device. However, generally, it is preferable that most, preferably all, of the chiral compounds present in the medium according to the present invention have the same sign in their HTP values.

[0300] Preferably, the chiral dopants present in the medium according to this application are mesogenic compounds, and most preferably, they exhibit a mesophase on their own.

[0301] In a preferred embodiment of the present invention, the medium comprises two or more chiral compounds, all having the same arithmetic sign of HTP.

[0302] The temperature dependence of the HTP of individual compounds can be high or low. The temperature dependence of the pitch of the medium can be compensated for by mixing compounds with different HTP temperature dependencies in corresponding ratios.

[0303] As for optically active ingredients, a number of commercially available chiral dopants are available to those skilled in the art, such as cholesteryl nonanoate, R- and S-811, R- and S-1011, R- and S-2011, R- and S-3011, R- and S-4011, or CB15 (all from Merck, Darmstadt).

[0304] Particularly suitable dopants are compounds containing one or more chiral groups and one or more mesogenic groups, or one or more aromatic or alicyclic groups that form a mesogenic group together with a chiral group.

[0305] Suitable chiral groups include, for example, chiral branched hydrocarbon groups, chiral ethanediols, binaphthols or dioxolanes, as well as monovalent or polyvalent chiral groups selected from the group consisting of sugar derivatives, sugar alcohols, sugar acids, lactic acid, chiral-substituted glycols, steroid derivatives, terpene derivatives, amino acids, or sequences of several, preferably 1 to 5, amino acids.

[0306] Preferred chiral groups include sugar derivatives, such as glucose, mannose, galactose, fructose, arabinose, and dextrose; sugar alcohols, such as sorbitol, mannitol, isitol, galactitol, or their anhydro derivatives, particularly dianhydrohexitol, such as dianhydrosorbide (1,4:3,6-dianhydro-D-sorbide, isosorbide), dianhydromannitol (isosorbitol), or dianhydroiditol (isoiditol); sugar acids, such as gluconic acid, gulonic acid, and ketoguronic acid; and chiral-substituted glycol groups. For example, mono- or oligoethylene or propylene glycol in which one or more CH2 groups are substituted with alkyl or alkoxy groups; amino acids, such as alanine, valine, phenylglycine or phenylalanine, or sequences of 1 to 5 of these amino acids; steroid derivatives, such as cholesteryl or cholic acid groups; terpene derivatives, such as menthyl, neomentyl, campheyl, pinail, terpineil, isolongifolyl, phenthyl, kalyl, myrtenyl, nopyl, geranyl, linaloyl, neryl, citronellyl or dihydrocitronellyl.

[0307] The medium according to the present invention preferably comprises a chiral dopant selected from the group of known chiral dopants. Suitable chiral groups and mesogenic chiral compounds are described, for example, in German Patent Nos. 3425503, 3534777, 3534778, 3534779, and 3534780, 4342280, European Patent No. 01038941, and German Patent No. 19541820. Other examples are the compounds listed in Table F below.

[0308] The chiral compounds preferably used in accordance with the present invention are selected from the group consisting of the formulas shown below.

[0309] Chiral dopants selected from the group consisting of compounds of the following formulas AI~A-III and A-Ch are particularly preferred.

[0310] [ka]

[0311] During the ceremony, R a11 , R a12 and R b12 This represents an alkyl group having 1 to 15 C atoms independently of each other, where furthermore, one or more non-adjacent CH2 groups are independently of each other such that the O and / or S atoms are not directly bonded to each other, -C(R z )=C(R z )-, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O-, where one or more H atoms may be replaced by F, Cl, Br, I or CN. Preferably, it represents alkyl, more preferably n-alkyl, however, R a12 is R b12 Unlike, R a21 and R a22This represents an alkyl group having 1 to 15 C atoms independently of each other, where furthermore, one or more non-adjacent CH2 groups are independently of each other such that the O and / or S atoms are not directly bonded to each other, -C(R z )=C(R z )-, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O-, where one or more H atoms may be replaced by F, Cl, Br, I or CN. Preferably both represent alkyl, more preferably n-alkyl. R a31 , R a32 and R b32 This represents a linear or branched alkyl group having 1 to 15 C atoms independently of each other, where furthermore, one or more non-adjacent CH2 groups are independently of each other such that the O and / or S atoms are not directly bonded to each other, and -C(R z )=C(R z )-, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O-, where one or more H atoms may be replaced by F, Cl, Br, I or CN. Preferably, it represents alkyl, more preferably n-alkyl, however, R a32 is R b32 Unlike, R z represents H, CH3, F, Cl, or CN, preferably H or F. R 8 This is the R given above. a11 One of the meanings is an alkyl group having 1 to 15 C atoms, more preferably an n-alkyl group. Z 8 This represents -C(O)O-, -CH2O-, -CF2O- or a single bond, preferably -C(O)O-. A 11 A is below 12 As defined in, or [ka] This represents, A 12 teeth, [ka] Preferably [ka] This represents, During the ceremony, L 12 Each instance independently represents a halogen, CN, or an alkyl, alkenyl, alkoxy, or alkenyloxy having up to 12 C atoms, wherein one or more H atoms may be replaced by a halogen, preferably methyl, ethyl, Cl, or F, and particularly preferably F. A 21 teeth, [ka] This represents, A 22 is, A 12 It has meaning to be given to, A 31 is, A 11 It has meaning to be given to, or [ka] This represents, A 32 is, A 12 It has meaning to be given to, n2 is 0, 1, or 2, and is either the same or different in each occurrence. n3 is 1, 2, or 3. r is 0, 1, 2, 3, or 4.

[0312] A dopant selected from the group consisting of compounds of the following formula is particularly preferred.

[0313] [ka]

[0314] [ka]

[0315] During the ceremony, m is an integer from 1 to 9, and n is an integer between 2 and 9, which may be the same or different in each occurrence.

[0316] Particularly preferred compounds of formula A are those of formula A-III.

[0317] Further preferred dopants are derivatives of isosorbide, isomannitol, or isoiditol of the following formulas A-IV.

[0318] [ka]

[0319] In the formula, the group [ka] teeth, [ka] The most preferred is dianhydrosorbitol.

[0320] Furthermore, it includes chiral ethanediols such as diphenylethanediol (hydrobenzoin), particularly mesogenic hydrobenzoin derivatives of the following formula AV, which are (S,S) enantiomers not shown.

[0321] [ka]

[0322] During the ceremony, [ka] Each of these is 1,4-phenylene or 1,4-cyclohexylene, which may be monosubstituted, disubstituted, or trisubstituted at L, independently of each other. L is H, F, Cl, CN, or an alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl or alkoxycarbonyloxy having 1 to 7 carbon atoms that may be halogenated. c is either 0 or 1. X is either CH2 or -C(O)-, Z 0 These are -COO-, -OCO-, -CH2CH2-, or single bonds. R 0 These are alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, or alkylcarbonyloxy compounds having 1 to 12 carbon atoms.

[0323] This is an example of a compound of formula IV.

[0324] [ka]

[0325] [ka]

[0326] Compounds of formulas A-IV are described in International Publication No. 98 / 00428. Compounds of formula AV are described in British Patent Application Publication No. 2,328,207.

[0327] Particularly preferred dopants are the chiral binaphthyl derivatives described in International Publication No. 02 / 94805, the chiral binaphthol acetal derivatives described in International Publication No. 02 / 34739, the chiral TADDOL derivatives described in International Publication No. 02 / 06265, and the chiral dopants having at least one fluorinated crosslinking group and a terminal or central chiral group described in International Publication Nos. 02 / 06196 and International Publication No. 02 / 06195.

[0328] Chiral compounds of formulas A-VI are particularly preferred.

[0329] [ka]

[0330] During the ceremony, X 1 , X 2 , Y 1 and Y 2 Each of these groups is independently of the others, and consists of F, Cl, Br, I, CN, SCN, SF5, and linear or branched alkyl groups having 1 to 25 carbon atoms (which may be monosubstituted or polysubstituted with F, Cl, Br, I, or CN, where furthermore, one or more non-adjacent CH2 groups are independently of each other, such that the O and / or S atoms are not directly bonded to each other, and consist of -O-, -S-, -NH-, NR 0 -, -CO-, -COO-, -OCO-, -OCOO-, -S-CO-, -CO-S-, -CH=CH- or -C≡C- (which may be replaced by a polymerizable group or a cycloalkyl or aryl having up to 20 carbon atoms (which may be monosubstituted or polysubstituted with a halogen, preferably F, or a polymerizable group), x 1 and x 2 Each of these is independently 0, 1, or 2. y 1 and y 2 Each of these is independently 0, 1, 2, 3, or 4. B 1 and B 2 Each of these is an aromatic, partially saturated, or fully saturated aliphatic six-membered ring, where one or more CH groups may be replaced by N atoms, and one or more non-adjacent CH2 groups may be replaced by O and / or S atoms. W 1 and W 2 These are, independently of each other, -Z 1 -A1 -(Z 2 -A 2 ) m -R, or one of the two is R 1 Or A 3 However, neither is H at the same time, or [ka] teeth, [ka] And, U 1 and U 2 Each of these is independently CH2, O, S, CO, or CS. V 1 and V 2 Each of them is independent of the other, (CH2) n (Here, 1 to 4 non-adjacent CH2 groups may be replaced by O and / or S), V 1 and V 2 One of them is, [ka] but, [ka] If that is the case, both are single bonds, n is 1, 2, or 3. Z 1 and Z 2 These are -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, and -CO-NR, each independent of the others. 0 -, -NR 0-CO-, -O-CH2-, -CH2-O-, -S-CH2-, -CH2-S-, -CF2-O-, -O-CF2-, -CF2-S-, -S-CF2-, -CH2-CH2-, -CF2-CH2-, -CH2-CF2-, -CF2-CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C-, two combinations of these groups (where two O and / or S and / or N atoms are not directly bonded to each other), (preferably -CH=CH-COO- or -COO-CH=CH-), or single bonds, R x This represents an alkyl group having 1 to 6 carbon atoms. A 1 , A 2 and A 3 Each of these is independently 1,4-phenylene, in which one or two non-adjacent CH groups may be replaced by N; 1,4-cyclohexylene, 1,3-dioxolane-4,5-diyl, 1,4-cyclohexenylene, 1,4-bicyclo[2.2.2]octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, or 1,2,3,4-tetrahydronaphthalene-2,6-diyl (each of these groups may be monosubstituted or polysubstituted with L); and further A 1 It can be a single bond, L is a halogen atom, preferably F, CN, NO2, an alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl or alkoxycarbonyloxy having 1 to 7 carbon atoms (where one or more H atoms may be replaced by F or Cl), m is independently 0, 1, 2, or 3. R and R 1Each of these is independently a linear or branched alkyl group having 1 or 3 to 25 carbon atoms, consisting of H, F, Cl, Br, I, CN, SCN, SF5 (which may be monosubstituted or polysubstituted with F, Cl, Br, I, or CN, and one or more non-adjacent CH2 groups are -O-, -S-, -NH-, -NR such that two O and / or S atoms are not directly bonded to each other). 0 -, -CO-, -COO-, -OCO-, -O-COO-, -S-CO-, -CO-S-, -CH=CH- or -C≡C- may be substituted, or it is a polymerizable group.

[0331] Chiral binaphthyl derivatives of formula A-VI-1 are particularly preferred.

[0332] [ka]

[0333] In the formula, rings B, R 0 and Z 0 This is as defined for equations A-IV and AV, where b is 0, 1, or 2.

[0334] In particular, it must be selected from the following equations A-VI-1a to A-VI-1c.

[0335] [ka]

[0336] In the formula, rings B, R 0 and Z 0 This is as defined for equation A-VI-1, R 0 This is either as defined for formulas A-IV, or an alkyl group having H or 1 to 4 carbon atoms. b is 0, 1, or 2. Z 0 These are specifically -OC(O)- or single bonds.

[0337] The concentration of one or more chiral dopants (one or more) in the LC medium is preferably in the range of 0.001% to 20%, preferably 0.05% to 5%, more preferably 0.1% to 2%, and most preferably 0.5% to 1.5%. These preferred concentration ranges apply in particular to chiral dopants S-4011 or R-4011 (both manufactured by Merck) and chiral dopants having the same or similar HTP. For chiral dopants with a higher or lower absolute value of HTP compared to S-4011, these preferred concentrations must be decreased or increased proportionally, respectively, according to the ratio of their HTP values ​​to the HTP value of S-4011.

[0338] The pitch p of the LC medium or host mixture according to the present invention is preferably in the range of 5 to 50 μm, more preferably 8 to 30 μm, and particularly preferably 10 to 20 μm.

[0339] Preferably, the medium according to the present invention comprises a stabilizer selected from the group of compounds of formula ST-1 to ST-19.

[0340] [ka]

[0341] [ka]

[0342] [ka]

[0343] [ka]

[0344] [ka] During the ceremony, R ST represents an alkyl or alkoxy group having H and 1 to 15 C atoms, where furthermore, one or more non-adjacent CH2 groups in these groups are independently of each other such that the O atoms are not directly bonded to one another, and are -C≡C-, -CF2O-, -OCF2-, -CH=CH-, [ka] -O-, -CO-O- or -O-CO-O- may be substituted, and furthermore, one or more H atoms may be substituted with halogens. [ka] [ka] This represents, Z ST These each independently represent -CO-O-, -O-CO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-CH2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C-, or a single bond. L 1 and L 2 Each of these independently represents F, Cl, CF3, or CHF2. p is either 1 or 2. q is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0345] Among the compounds of formula ST, the compound shown below is particularly preferred.

[0346] [ka]

[0347] [ka]

[0348] [ka]

[0349] In the compounds of formulas ST-3a and ST-3b, n preferably represents 3. In the compound of formula ST-2a, n preferably represents 7.

[0350] A particularly very preferred mixture according to the present invention comprises one or more stabilizers from the group of compounds of formula ST-2a-1, ST-3a-1, ST-3b-1, ST-8-1, ST-9-1, and ST-12.

[0351] [ka]

[0352] [ka]

[0353] The compounds of formulas ST-1 to ST-19 are preferably present in the liquid crystal mixture according to the present invention in an amount of 0.005 to 0.5% based on the mixture.

[0354] When the mixture according to the present invention contains two or more compounds from the group of compounds of formula ST-1 to ST-18, the concentration increases to 0.01 to 1% relative to the mixture, corresponding to the case of two compounds.

[0355] However, the total proportion of compounds of formulas ST-1 to ST-18 based on the mixture according to the present invention should not exceed 2%.

[0356] The mixture according to the present invention is preferably, One or more compounds selected from the compounds of formula I, preferably formulas I-1, I-2, and I-3, are added in a total concentration preferably in the range of 0.1% to 10%, more preferably 0.5% to 8% or 1% to 5%, and particularly preferably 2% to 4%. and / or One or more compounds of formula IIA are preferably used in a total concentration of 5% to 30%, more preferably 7% to 25%, and particularly preferably 10% to 20%. and / or • One or more compounds of formulas IIA and IIB, preferably in a total concentration within the range of 30% to 45%, and / or • One or more compounds of formulas I and IV are preferably used in a total concentration within the range of 35% to 60%, more preferably 40% to 55%, and particularly preferably 45% to 50%. and / or One or more compounds of formula I, as well as formulas IV and IVb, are preferably in a total concentration within the range of 35% to 70%, more preferably 40% to 65%, and particularly preferably 45% to 60%. and / or • One or more compounds of formulas IIA, IIB, and III-2 are used in a total concentration preferably in the range of 30% to 65%, more preferably 35% to 60%, and particularly preferably 40% to 55%. Includes.

[0357] In particular, the media • One or more compounds CY-n-Om, particularly CY-3-O4, CY-5-O and / or CY-3-O2, in a total concentration preferably in the range of 5% to 30%, preferably 10% to 20%. and / or CPY-n-Om, particularly CPY-2-O2, CPY-3-O2 and / or CPY-5-O2, preferably in a concentration of more than 5%, and especially 7% to 20%, relative to the whole mixture. and / or • One or more compounds CCY-n-Om, preferably CCY-4-O2, CCY-3-O2, CCY-3-O3, CCY-3-O1 and / or CCY-5-O2, are added to the mixture at a concentration of preferably more than 3%, and particularly 5% to 15%, based on the total amount of the mixture. and / or CLY-n-Om, preferably CLY-2-O4, CLY-3-O2 and / or CLY-3-O3, at a concentration of preferably more than 5%, and particularly 10% to 30%, relative to the whole mixture. and / or CPY-n-Om and CY-n-Om are added at a concentration of preferably 10% to 80% of the total mixture. and / or CPY-n-Om and PY-n-Om, preferably CPY-2-O2 and / or CPY-3-O2 and PY-3-O2 or PY-1-O2, are used in a concentration of preferably 5-20%, more preferably 10-15%, relative to the entire mixture. and / or CCVC-nV, preferably CCVC-3-V, is added to the entire mixture at a concentration of preferably 2-10%. and / or • Add CC-VV at a concentration of preferably 5-50% of the total mixture. and / or A compound of formula CC-3-V1 and / or CC-4-V1 (one or more types) is used in a total concentration preferably in the range of 5-40%, more preferably 15-35%, and particularly preferably 20-30%. and / or One or more compounds of the formula B-nO-Om and / or B(S)-nO-Om, particularly compound B(S)-2O-O5, preferably in a concentration of 2-10%, and compound CC-3-V1 and / or compound CC-4-V1, in a total concentration of 10-30%, preferably in a total concentration of 15-20%. and / or • 0.1% to 3% of compound PPGU-3-F, and / or ·Compound B(S)-(c5)1O-O2 [ka] Includes.

[0358] The present invention further comprises the liquid crystal medium described in claim 1 as a dielectric, and is characterized in that the display is a VA, SA-VA, IPS, U-IPS, FFS, UB-FFS, SA-FFS, PS-VA, PS-OCB, PS-IPS, PS-FFS, PS-UB-FFS, PS-positive-VA, PS-TN, polymer-stabilized SA-VA, or polymer-stabilized SA-FFS display, and has an active matrix addressing electro-optical display.

[0359] The liquid crystal medium according to the present invention is advantageous in that it preferably has a nematic phase with a temperature range of -20°C or lower to 70°C or higher, particularly preferably -30°C or lower to 80°C or higher, and very particularly preferably -40°C or lower to 90°C or higher.

[0360] The medium according to the present invention has a transparency temperature of 70°C or higher, preferably 74°C or higher.

[0361] The expression "having a nematic phase" means, on the one hand, that the smectic phase and crystallization are not observed at temperatures lower than the corresponding temperature, and on the other hand, that transparency still does not occur upon heating from the nematic phase. Low-temperature studies are performed using a fluid viscometer at the corresponding temperature and confirmed by storing the sample for at least 100 hours in a test cell with a layer thickness suitable for electro-optical applications. If the storage stability in the test cell at -20°C is 1000 hours or more, the medium is said to be stable at this temperature. For temperatures of -30°C and -40°C, the corresponding times are 500 hours and 250 hours, respectively. At high temperatures, the transparency point is measured in a capillary tube using conventional methods.

[0362] The liquid crystal mixture preferably has a nematic phase range of at least 60K and a maximum of 30mm at 20°C. 2 ·Seconds -1 The fluid viscosity ν 20It has.

[0363] The mixture is nematic at temperatures below -20°C, preferably below -30°C, and very preferably below -40°C.

[0364] The birefringence Δn value in liquid crystal mixtures is generally between 0.07 and 0.16, preferably between 0.08 and 0.15, and very preferably between 0.09 and 0.14.

[0365] In a preferred embodiment of the present invention, the medium has a birefringence in the range of 0.090 to 0.110, preferably 0.095 to 0.105, and particularly 0.100 to 0.105.

[0366] In another preferred embodiment, the medium according to the present invention has a birefringence of 0.120 or higher, preferably in the range of 0.125 to 0.145, and more preferably in the range of 0.130 to 0.140.

[0367] The liquid crystal mixture according to the present invention has a dielectric anisotropy Δε of -1.5 to -8.0, preferably -2.0 to -4.0, and particularly -2.5 to -3.5.

[0368] The rotational viscosity γ1 at 20°C is preferably 120 mPa·s or less, and particularly 100 mPa·s or less.

[0369] In a preferred embodiment, the rotational viscosity γ1 at 20°C is 100 mPa·s or less, and particularly 95 mPa·s or less.

[0370] The liquid crystal medium according to the present invention has a relatively low threshold voltage (V0). These are preferably in the range of 1.7V to 3.0V, particularly preferably 2.7V or less, and very particularly preferably 2.5V or less.

[0371] In this invention, unless otherwise specified, the term "threshold voltage" refers to the capacitance threshold (V0), also known as the Fredericks threshold.

[0372] In addition, the liquid crystal medium according to the present invention has a high voltage retention rate in liquid crystal cells.

[0373] Generally, liquid crystal media with a low address voltage or threshold voltage exhibit a lower voltage retention rate than those with a high address voltage or threshold voltage, and vice versa.

[0374] In this invention, the term "dielectrically positive compound" refers to a compound having a Δε greater than 1.5, the term "dielectrically neutral compound" refers to a compound having a Δε between -1.5 and 1.5, and the term "dielectrically negative compound" refers to a compound having a Δε less than -1.5. The dielectric anisotropy of a compound is determined by dissolving 10% of the compound in a liquid crystal host and measuring the capacitance of the mixture obtained in at least one test cell with a homeotropic and homogeneous surface orientation, each having a layer thickness of 20 μm, at 1 kHz. The measurement voltage is typically 0.5V to 1.0V, but is always lower than the capacitance threshold of the liquid crystal mixture under consideration.

[0375] All temperature values ​​shown in this invention are in °C.

[0376] The mixtures according to the present invention are suitable for all VA-TFT applications, such as VAN, MVA, (S)-PVA, ASV, PSA (polymer sustained VA), and PS-VA (polymer stabilized VA). They are also suitable for IPS (in-plane switching) and FFS (fringe field switching) applications with negative Δε.

[0377] The nematic liquid crystal mixture in the display according to the present invention generally contains two types of components A and B, which themselves consist of one or more individual compounds.

[0378] Component A has significantly negative dielectric anisotropy, giving the nematic phase a dielectric anisotropy of -0.5 or less. In addition to one or more compounds of formula I, component A preferably includes compounds of formulas IIA, IIB and / or IIC, and further one or more compounds of formula IV-1.

[0379] The proportion of component A is preferably between 45% and 100%, and particularly between 60% and 85%.

[0380] For component A, preferably one (or more) individual compounds having a Δε value of -0.8 or less are selected. This value must be more negative, and the smaller the proportion of A in the whole mixture, the smaller the value must be.

[0381] Component B exhibits significant nematogenic properties and 30 mm at 20°C. 2 ·Seconds -1 The following is preferably 25 mm 2 ·Seconds -1 It has the following flow viscosity.

[0382] Numerous suitable materials are known to those skilled in the art from the literature. Compounds of formula O-17 are particularly preferred.

[0383] Particularly preferred individual compounds in component B are 18 mm at 20°C. 2 ·Seconds -1 The following is preferably 12 mm 2 ·Seconds -1 This is an extremely low viscosity nematic liquid crystal having the following fluid viscosity.

[0384] Component B is unidirectional or enantiomerically nematic, does not have a smectic phase, and can prevent the formation of a smectic phase in liquid crystal mixtures down to very low temperatures. For example, when various highly nematogenic materials are added to a smectic liquid crystal mixture, the nematogenicity of these materials can be compared through the degree of smectic phase suppression achieved.

[0385] The mixture may also contain component C, which includes a compound having a dielectric anisotropy Δε of 1.5 or greater. These so-called positive compounds are generally present in the mixture with negative dielectric anisotropy in an amount of 20% by weight or less, based on the entire mixture.

[0386] In addition to one or more compounds of formula I, the phase preferably includes 4 to 15 types, particularly 5 to 12 types, and especially preferably fewer than 10 types of compounds of formula IIA, IIB and / or IIC, and optionally one or more compounds of formula IV-1.

[0387] In addition to the compound of formula IB and the compounds of formulas IIA, IIB and / or IIC, and optionally IV-1, other components may be present in amounts up to, for example, 45% of the total mixture, but preferably up to 35%, and particularly up to 10%.

[0388] Other components are preferably selected from azoxybenzene, benzylideneaniline, biphenyl, terphenyl, phenyl or cyclohexyl benzoate, phenyl or cyclohexylcyclohexane carboxylate, phenylcyclohexane, cyclohexyl biphenyl, cyclohexyl cyclohexane, cyclohexyl naphthalene, 1,4-biscyclohexyl biphenyl or cyclohexylpyrimidine, phenyl or cyclohexyl dioxane, optionally halogenated stilbene, benzylphenyl ether, tran and substituted cinnamic acid esters, particularly known substances.

[0389] The most important compounds suitable as components of this type of liquid crystal phase can be characterized by formula IV. [ka]

[0390] In the formula, L and E represent carbocyclic or heterocyclic systems from the group formed by 1,4-disubstituted benzenes and cyclohexane rings, 4,4'-disubstituted biphenyls, phenylcyclohexane and cyclohexylcyclohexane systems, 2,5-disubstituted pyrimidines and 1,3-dioxane rings, 2,6-disubstituted naphthalenes, di and tetrahydronaphthalenes, quinazolines and tetrahydroquinazolines, respectively. G is -CH=CH-, -N(O)=N-, -CH=CQ-, -CH=N(O)-, -C≡C-, -CH2-CH2-, -CO-O-, -CH2-O-, -CO-S-, -C Represents H2-S-, -CH=N-, -COO-Phe-COO-, -CF2O-, -CF=CF-, -OCF2-, -OCH2-, -(CH2)4-, -(CH2)3O-, Alternatively, CC represents a single bond, Q represents a halogen, preferably chlorine or -CN, and R 20 and R 21 Each represents an alkyl, alkenyl, alkoxy, alkoxyalkyl, or alkoxycarbonyloxy group having up to 18, preferably up to 8, carbon atoms, or one of these groups represents CN, NC, NO2, NCS, CF3, SF5, OCF3, F, Cl, or Br.

[0391] In most of these compounds, R 20 and R 21 These groups are distinct from one another, and one of these groups is usually an alkyl or alkoxy group. Other variants of the proposed substituents are also common. Many such substances or mixtures thereof are commercially available. All of these substances can be prepared by methods known from the literature.

[0392] It goes without saying to those skilled in the art that the VA, IPS, or FFS mixture of the present invention may also include, for example, compounds in which H, N, O, Cl, and F are substituted with the corresponding isotopes.

[0393] The compound of formula P is optionally added to the mixture according to the present invention, based on the mixture, preferably at a concentration of 0.01 to 5% by weight, and particularly preferably 0.2 to 2% by weight. These mixtures may optionally include an initiator, as described, for example, in U.S. Patent No. 6,781,665. The initiator, for example, Irganox-1076 from BASF, is preferably added to the mixture containing the polymerizable compound in an amount of 0 to 1%. This type of mixture can be used in so-called polymer-stabilized VA (PS-VA) or polymer-sustained VA (PSA), but the polymerization of the reactive mesogen is intended to take place in the liquid crystal mixture after the display panel has been filled. The prerequisite here is that the liquid crystal compound of the LC host does not react under the polymerization conditions of the reactive mesogen, i.e., exposure to UV in the wavelength range of generally 320 to 360 nm. For example, liquid crystal compounds containing alkenyl side chains, such as CC-3-V, do not react under the polymerization conditions of RM (UV polymerization); therefore, in this specification, such compounds are not considered RM.

[0394] The compounds according to the present invention can be synthesized by known methods described in the literature (e.g., standard works such as Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, and Stuttgart) or similar methods under known reaction conditions suitable for the aforementioned reactions. Variations known to themselves, though not mentioned herein, can also be used herein. In particular, they can be prepared by methods described in or similar to the following reaction schemes. Further methods for preparing the compounds of the present invention can be obtained from the examples.

[0395] Other mesogenic compounds not explicitly mentioned above can also be advantageously used in media according to the present invention. Such compounds are known to those skilled in the art.

[0396] The following examples illustrate the present invention without limiting it. However, they will be helpful to those skilled in the art to understand preferred mixing concepts, along with preferred compounds, their respective concentrations, and combinations thereof. In addition, the examples illustrate the available properties and combinations of properties.

[0397] In the present invention and the following examples, the structure of the liquid crystal compound is indicated by an acronym, and its conversion to a chemical formula is performed according to Tables A to C below. n H 2n+1 , C m H 2m+1 and C l H2 l+1 or C n H 2n and C m H 2m These are linear alkyl or alkylene groups having n, m, and l carbon atoms, respectively. Preferably, n, m, and l are 1, 2, 3, 4, 5, 6, or 7, independently of each other. Table A shows the codes of the ring elements of the core of the compound, Table B lists the bridging units, and Table C lists the meanings of the symbols of the left- and right-end groups of the molecule. The acronym consists of the code of the ring element having any linking group, followed by a first hyphen and the code of the left-end group, and a second hyphen and the code of the right-end group. Table D shows structural examples of the compound along with their respective abbreviations.

[0398] <Table A: Ring elements>

[0399] [Table 3]

[0400] [Table 4]

[0401] [Table 5]

[0402] <Table B: Bridge Units>

[0403] [Table 6]

[0404] <Table C: Terminal group>

[0405] [Table 7]

[0406] [Table 8]

[0407] In the table, n and m are integers, and the three dots "..." are spaces for other abbreviations from this table.

[0408] Apart from the compounds of formulas I, IIA, IIB, IIC, and / or IID, the mixture according to the present invention preferably comprises one or more compounds of the compounds described below.

[0409] Use the following abbreviations: (n, m, k, and l are each independent integers, preferably 1 to 9, preferably 1 to 7, and k and l may also be 0, preferably 0 to 4, more preferably 0 or 2, most preferably 2; n is preferably 1, 2, 3, 4, or 5, and in the combination "-nO-", preferably 1, 2, 3, or 4, more preferably 2 or 4; m is preferably 1, 2, 3, 4, or 5, and in the combination "-Om", preferably 1, 2, 3, or 4, more preferably 2 or 4; the combination "-lVm" is preferably "2V1".)

[0410]

[0411] [Table 9]

[0412] Table 10

[0413] Table 11

[0414] Table 12

[0415] Table 13

[0416] Table 14

[0417] Table 15

[0418] Table 16

[0419] Table 17

[0420] Table 18

[0421] Table 19

[0422] [Table 20]

[0423] [Table 21]

[0424] [Table 22]

[0425] [Table 23]

[0426] [Table 24]

[0427] [Table 25]

[0428] [Table 26]

[0429] [Table 27]

[0430] Table E shows the chiral dopants that can be added to the LC medium according to the present invention.

[0431] [Table 28]

[0432] [Table 29]

[0433] [Table 30]

[0434] [Table 31]

[0435] [Table 32]

[0436] Table F shows exemplary reactive mesogenic compounds (RM) that can be used with the LC medium according to the present invention.

[0437] [Table 33]

[0438] [Table 34]

[0439] [Table 35]

[0440] [Table 36]

[0441] [Table 37]

[0442] [Table 38]

[0443] Table 39

[0444] Table 40

[0445] Table 41

[0446] Table 42

[0447] Table 43

[0448] Table 44

[0449] Table 45

[0450] Table 46

[0451] Table 47

[0452] Table 48

[0453] Table 49

[0454] Table 50

[0455] Table 51

[0456] Table 52

[0457] Table 53

[0458] Table 54

[0459] Table 55

[0460] Table 56

[0461] In a preferred embodiment, the mixture according to the present invention preferably comprises one or more polymerizable compounds selected from polymerizable compounds of formulas RM-1 to RM-144. Of these, compounds RM-1, RM-4, RM-8, RM-17, RM-19, RM-35, RM-37, RM-39, RM-40, RM-41, RM-48, RM-52, RM-54, RM-57, RM-64, RM-74, RM-76, RM-88, RM-102, RM-103, RM-109, RM-117, RM-120, RM-121, RM-122, and RM-145 to RM-153 are particularly preferred.

[0462] In another preferred embodiment, the mixture according to the present invention comprises one or more polymerizable compounds selected from formulas RM-145 to RM-152, and very preferably from formulas RM-147 to RM-152.

[0463] Table G shows self-aligning additives for vertical orientation that can be used in LC media for SA-VA and SA-FFS displays according to the present invention, together with polymerizable compounds of formula P.

[0464] [Table 57]

[0465] [Table 58]

[0466] [Table 59]

[0467] [Table 60]

[0468] [Table 61]

[0469] [Table 62]

[0470] [Table 63]

[0471] [Table 64]

[0472] [Table 65]

[0473] [Table 66]

[0474] [Table 67]

[0475] [Table 68]

[0476] [Table 69]

[0477] In a preferred embodiment, the LC medium, SA-VA, and SA-FFS display according to the present invention is combined with one or more RMs of formula P and comprises one or more SA additives selected from formulas SA-1 to SA-48, preferably from formulas SA-14 to SA-48, and very preferably from formulas SA-20 to SA-34 and SA-44. [Examples]

[0478] The following examples are intended to illustrate the invention without limiting it. In the examples, mp represents the melting point, and T (N,I) The transparent point of the liquid crystal material is expressed in Celsius. Furthermore, C represents the crystalline solid state, S represents the smectic phase (the subscript indicates the type of phase), N represents the nematic state, Ch represents the cholesteric phase, I represents the isotropic phase, and T represents the transparent point of the liquid crystal material in Celsius. g The symbol represents the glass transition temperature. The number between the two symbols indicates the conversion temperature in Celsius.

[0479] The host mixture used to measure the optical anisotropy Δn of a single compound is the commercially available mixture ZLI-4792 (Merck). The dielectric anisotropy Δε is determined using the commercially available mixture ZLI-2857. The physical data of the compound under consideration is obtained from the change in the dielectric constant of the host mixture after adding the compound under consideration and from extrapolation to 100% of the compound being considered. Generally, 10% of the compound under consideration is dissolved in the host mixture, depending on its solubility.

[0480] Unless otherwise indicated, part or percentage data represents parts by weight or percentage by weight.

[0481] Up and down: V0 represents the capacitance threshold voltage [V] at 20°C. n e This represents the anomalous refractive index at 20°C and 589nm. n0 represents the typical refractive index at 20°C and 589nm. Δn represents the optical anisotropy at 20°C and 589 nm. ε ⊥ This represents the dielectric constant perpendicular to the director at 20°C and 1kHz. ε ∥ This represents the dielectric constant parallel to the director at 20°C and 1kHz. Δε represents the dielectric anisotropy at 20°C and 1kHz. cl.p. and T(N,I) represent the point of transparency [°C]. γ1 is the rotational viscosity [mPa·s] at 20°C, K1 represents the elastic constant [pN] for "splay" deformation at 20°C. K2 represents the elastic constant [pN] for "twist" deformation at 20°C. K3 represents the elastic constant [pN] for "bend" deformation at 20°C, and LTS (low-temperature stability) refers to low-temperature stability (nematic phase) and is determined in either a test cell or bulk.

[0482] Unless otherwise specified, all temperature values ​​expressed in this application, such as the melting point T(C,N), the transition from the smectic (S) phase to the nematic (N) phase T(S,N), and the transparency point T(N,I), are expressed in degrees Celsius (°C).

[0483] In this invention, the term "threshold voltage" refers to the capacitance threshold (V0), also known as the Frederick's threshold, unless otherwise specified. Furthermore, in the example, although generally typical, 10% relative contrast (V0) is used. 10 The optical threshold for ) may also be indicated.

[0484] The display used for measuring capacitance threshold voltage consists of two flat, parallel glass outer plates separated by a 20 μm gap. Each outer plate has an electrode layer on the inside and an unrubbed polyimide orientation layer on top, which causes homeotropic edge orientation of liquid crystal molecules.

[0485] The display or test cell used for measuring the tilt angle consists of two flat, parallel glass outer plates separated by a 4 μm gap, each having an electrode layer on the inside and a polyimide orientation layer on top, however, the two polyimide layers are rubbed in opposite parallel directions to each other, resulting in homeotropic edge orientation of liquid crystal molecules.

[0486] Polymerizable compounds polymerize within a display or test cell by simultaneously applying a voltage to the display (typically 10V-30V AC, 1kHz) and irradiating it with UV light of a specified intensity for a predetermined time. In the examples, unless otherwise indicated, an intensity of 100mW / cm² is used for polymerization. 2 A metal halide lamp is used. The intensity is measured using a standard meter (a high-frequency Hoenle UV meter equipped with a UV sensor).

[0487] The tilt angle is determined using the Axometrics AxoScan Mueller matrix polarimeter. Here, a low value (i.e., a large deviation from 90°) corresponds to a large tilt.

[0488] Unless otherwise specified, the term “tilt angle” refers to the angle between the LC director and the substrate, and “LC director” refers to the preferred orientation direction of the optical principal axes of LC molecules in a uniformly oriented layer of LC molecules. In the case of calamitic, i.e., uniaxial and positively birefringent LC molecules, “LC director” corresponds to the molecular long axis of the LC molecule.

[0489] Unless otherwise clearly stated, VHR is 20℃ (VHR 20 ) and after 5 minutes in a 100°C oven (VHR 100 This is determined in the equipment model LCM-1(O0004) commercially available from Toyo Technica Co., Ltd. in Japan. Unless otherwise specified, the voltage used has a frequency in the range of 1Hz to 60Hz.

[0490] The accuracy of VHR measurement depends on the individual VHR value. Accuracy decreases as the value decreases. The following table summarizes the commonly observed deviations for values ​​within various dimensional ranges, ordered by VHR magnitude.

[0491] [Table 70]

[0492] The stability against UV irradiation will be examined using the Heraeus "Suntest CPS+" system from Germany, which utilizes a xenon lamp NXE1500B. Sealed test cells will be irradiated for 2.0 hours without additional heating unless otherwise specified. The irradiation power in the wavelength range of 300nm to 800nm ​​will be 765W / m². 2 V. To simulate the so-called window glass mode, a UV "cutoff" filter with an edge wavelength of 310 nm is used. In each series of experiments, at least four test cells are examined for each condition, and the results are presented as the average of the corresponding individual measurements.

[0493] For example, the decrease in voltage holding ratio (ΔVHR) typically caused by UV irradiation or exposure to LCD backlights is determined according to the following equation (1).

[0494]

number

[0495] To investigate the low-temperature stability, also known as "LTS (low-temperature stability)," i.e., the stability of bulk LC mixtures against spontaneous crystallization or smectic phase formation of individual components at low temperatures, several sealed bottles, each containing approximately 1 g of material, are stored at one or more predetermined temperatures, typically -10°C, -20°C, -30°C, and / or -40°C, and visually inspected at regular intervals to see if a phase transition is observed. The time is recorded when the first sample shows a change at a predetermined temperature. The time until the last inspection in which no change is observed is recorded as the respective LTS.

[0496] The ion density for calculating resistivity is measured using the LC material property measurement system Model 6254, commercially available from Toyo Technica Co., Ltd. in Japan, with a VHR test cell (cell gap 3.2 μm) using AL16301 polyimide (JSR Corporation, Japan). The measurement is performed after storing the sample in an oven at 60°C or 100°C for 5 minutes.

[0497] The term "HTP" refers to the helical twist force (in μm) of an optically active or chiral substance in an LC medium. Unless otherwise specified, HTP is measured at 20°C in the commercially available nematic LC host mixture MLD-6260 (Merck).

[0498] The transparency point is measured using a Mettler Thermosystem FP900. Optical anisotropy (n) is measured using an Abbe refractometer H005 (sodium spectral lamp Na10, 589 nm, at 20°C). Dielectric anisotropy (Δε) is measured at 20°C using an LCR meter E4980A / Agilent (G005) (ε-parallel cell equipped with JALS2096-R1). Start-up voltage (V0) is measured at 20°C using an LCR meter E4980A / Agilent (G005) (ε-parallel cell equipped with JALS2096-R1). Rotational viscosity (γ1) is measured at 20°C using a Toyo Technica LCM-2 (0002) (gamma 1 negative cell equipped with JALS-2096-R1). The elastic constant (K1, spray) is measured at 20°C using an LCR meter E4980A / Agilent Corporation (G005) (ε-parallel cell equipped with JALS2096-R1). K3: The elastic constant (K3, bend) is measured at 20°C using an LCR meter E4980A / Agilent Corporation (G005) (ε-parallel cell equipped with JALS2096-R1).

[0499] Unless otherwise explicitly stated, all concentrations in this specification are expressed as weight percentages of the entire corresponding mixture consisting of all solid or liquid crystal components, excluding the solvent. All physical properties are determined in accordance with "Merck Liquid Crystals, Physical Properties of Liquid Crystals," published November 1997, Merck, Germany, and a temperature of 20°C is applied unless otherwise expressly stated.

[0500] The following examples of mixtures having negative dielectric anisotropy are particularly suitable for IPS and FFS displays, especially liquid crystal displays having at least one planar alignment layer such as UB-FFS (ultra-high brightness FFS), as well as VA displays.

[0501] <Examples of mixtures and comparative examples> As shown in the table below, comparative mixtures C1-C4 and example mixtures M1-M95 were prepared and examined.

[0502] <Comparison mixture C1> [Table 71]

[0503] <Comparative mixture C2> [Table 72]

[0504] <Comparative mixture C3> [Table 73]

[0505] <Comparative mixture C4> [Table 74]

[0506] <Mixture example M1> [Table 75]

[0507] <Mixture M2> [Table 76]

[0508] <Mixture M3> [Table 77]

[0509] <Mixture M4> [Table 78]

[0510] <Mixture M5> [Table 79]

[0511] A comparison of the example mixtures M1-M5 with medium C1 demonstrates that the VHR of the liquid crystal medium according to the present invention is significantly improved.

[0512] <Mixture M6> [Table 80]

[0513] <Mixture M7> [Table 81]

[0514] <Mixture M8> [Table 82]

[0515] <Mixture M9> Table 83

[0516] <Mixture M10> Table 84

[0517] <Mixture M11> Table 85

[0518] <Mixture M12> Table 86

[0519] <Mixture M13> Table 87

[0520] <Mixture M14> Table 88

[0521] <Mixture M15> Table 89

[0522] <Mixture M16> Table 90

[0523] <Mixture M17> Table 91

[0524] Despite the remarkable stabilizing effect of the compound of formula I in the medium according to the present invention, the stability of the medium can be further improved, particularly against combined thermal and light loads, by using stabilizers.

[0525] The following mixtures M18 to M54 contain the stabilizers shown above. The amounts of host mixtures and stabilizers given in the table are added together to make 100% by weight.

[0526] <Table 1: Mixtures containing stabilizers> [Table 92]

[0527] [Table 93]

[0528] Chiral nematic mixture M55 consists of 99.20% mixture M18 and 0.80% chiral dopant S-2011. [ka]

[0529] Mixture M55 stands out for its extremely high stability under UV load and exhibits improved switch times.

[0530] <Mixture M56> [Table 94]

[0531] <Mixture M57> [Table 95]

[0532] <Mixture M58> Table 96

[0533] <Mixture M59> Table 97

[0534] <Mixture M60> Table 98

[0535] <Mixture M61> Table 99

[0536] <Mixture M62> Table 100

[0537] <Mixture M63> Table 101

[0538] <Mixture M64> Table 102

[0539] <Mixture M65> Table 103

[0540] <Mixture M66> Table 104

[0541] <Mixture M67> Table 105

[0542] <Mixture M68> Table 106

[0543] <Mixture M69> Table 107

[0544] <Mixture M70> Table 108

[0545] <Mixture M71> Table 109

[0546] <Mixture M72> Table 110

[0547] <Mixture M73> Table 111

[0548] <Mixture M74> Table 112

[0549] <Mixture M75> Table 113

[0550] <Mixture M76> Table 114

[0551] <Mixture M77> Table 115

[0552] <Mixture M78> Table 116

[0553] <Mixture M79> Table 117

[0554] <Mixture M80> Table 118

[0555] <Mixture M81> Table 119

[0556] <Mixture M82> Table 120

[0557] <Mixture M83> Table 121

[0558] <Mixture M84> Table 122

[0559] <Mixture M85> Table 123

[0560] <Mixed M86> Table 124

[0561] <Mixture M87> Table 125

[0562] <Mixture M88> Table 126

[0563] <Mixture M89> Table 127

[0564] <Mixture M90> Table 128

[0565] <Mixture M91> Table 129

[0566] <Mixture M92> [Table 130]

[0567] <Mixture M93> [Table 131]

[0568] <Mixture M94> [Table 132]

[0569] <Mixture M95> [Table 133]

[0570] The medium according to the present invention is particularly suitable for use in PS-VA displays, as shown in the following examples of use.

[0571] <Example of polymerizable mixture>

[0572] <Comparative mixture example CP1> Comparative mixture example CP1 consists of 99.595% comparative mixture C2, 0.40% compound RM-1, and 0.005% compound ST-3a-1. [ka] [ka]

[0573] <Comparative mixture example CP2> Comparative mixture example CP2 consists of 99.595% comparative mixture C3, 0.40% compound RM-1, and 0.005% compound ST-3a-1. [ka] [ka]

[0574] <Comparative mixture example CP3> Comparative mixture example CP3 consists of 99.595% comparative mixture C4, 0.40% compound RM-1, and 0.005% compound ST-3a-1. [ka] [ka]

[0575] <Mixture example P1> Mixture example P1 consists of 99.595% mixture M-10, 0.40% compound RM-1, and 0.005% compound ST-3a-1. [ka] [ka]

[0576] <Mixture example P2> Mixture example P2 consists of 99.595% mixture M-11, 0.40% compound RM-1, and 0.005% compound ST-3a-1.

[0577] <Mixture example P3> Mixture example P3 consists of 99.595% mixture M-12, 0.40% compound RM-1, and 0.005% compound ST-3a-1.

[0578] <Mixture example P4> Mixture example P4 consists of 99.595% mixture M-13, 0.40% compound RM-1, and 0.005% compound ST-3a-1.

[0579] <Mixture example P5> Mixture example P5 consists of 99.595% mixture M-14, 0.40% compound RM-1, and 0.005% compound ST-3a-1.

[0580] <Mixture example P6> Mixture example P6 consists of 99.595% mixture M-14, 0.40% compound RM-19, and 0.005% compound ST-3a-1. [ka]

[0581] <Mixture example P7> Mixture example P7 consists of 99.595% mixture M-14, 0.40% compound RM-19, and 0.005% compound ST-3b-1. [ka] [ka]

[0582] <Mixture example P8> Mixture example P8 consists of 99.595% mixture M-14, 0.40% compound RM-35, and 0.005% compound ST-3a-1. [ka] [ka]

[0583] <Usage example A> We will investigate the applicability of these media to VA-type polymer-stabilized displays (PS-VA).

[0584] The polymerizable mixture shown above is filled into a PSA test cell, and RM is polymerized under voltage application, and several properties such as the residual RM content, VHR after loading, and generation of tilt angle are measured.

[0585] <VHR Measurement> The VHR values of the polymerizable mixtures CP1, CP, and P5 are measured at 60 °C in a VA-VHR test cell before and after UV exposure for 80 minutes at room temperature using a fluorescent UV lamp type C (305 nm - 355 nm), followed by CCFL backlight (BL) loading up to 12 days. The results are shown in Table 2.

[0586]

Table 134

[0587] The compositions of the media CP1, CP2, and P5 are very similar in terms of physical parameters and mixture components, and differ only in the presence of the compound CLP-3-T. It can be seen from Table 2 that the initial VHR values of the polymerizable mixtures CP1, CP2, and P5 are at almost the same level. After UV exposure, mixtures CP1 and CP2 show a significant decrease in VHR, while medium P5 maintains a high VHR even after 12 days of backlight loading

[0588] Therefore, mixture P5, which has a higher VHR after UV exposure, is particularly suitable for PSA displays with high reliability and UV stability.

[0589] <Pretilt> In the PS-VA process, a tilt angle is generated by UV-initiated polymerization of the reactive mesogen. Each of the polymerizable mixtures CP3 and P5 is inserted into a VA e / o test cell. The test cell includes a VA-polyimide alignment layer (JALS-2096-R1) rubbed antiparallel. The thickness d of the LC layer is about μm.

[0590] The pretilt angle is 50 mW / cm 2After UV irradiation for up to 120 seconds (energy level 6J), the crystal rotation is determined by a crystal rotation experiment (Autronic-Melchers TBA-105). The results are shown in Table 3.

[0591] [Table 135]

[0592] The tilt angle generated by medium P5 is found to be equivalent to the value observed with the state-of-the-art comparison medium CP3.

[0593] <Polymerization rate> The polymerization rate is measured by determining the residual content (weight %) of unpolymerized RM in the mixture after UV exposure at a predetermined intensity and lamp spectrum after a predetermined UV exposure time. A smaller residual RM content after a predetermined time interval indicates faster polymerization. For this purpose, the polymerizable mixture is packed into an electro-optic test cell with a cell gap of 6-7 μm, made from soda-lime glass coated with an ITO layer approximately 200 nm thick and a Varitronix VA-polyimide layer 30 nm thick. The test cell is irradiated with a fluorescent UV lamp type C (305 nm-355 nm) to induce polymerization of RM. The irradiation times are given in the table below.

[0594] After polymerization, the test cell was opened, the mixture was dissolved in 2 ml of ethyl methyl ketone, and washed out of the test cell. The mixture was then analyzed by high-performance liquid chromatography (HPLC). The results are shown in Table 4.

[0595] [Table 136]

[0596] Table 4 shows that the polymerization rate of medium P5 according to the present invention is advantageously high, making it suitable for industrial applications.

Claims

1. One or more compounds of formula I, and It comprises one or more compounds selected from the group of compounds of formulas IIA, IIB, IIC, and IID, It has a negative dielectric anisotropy Δε, However, mixtures X-1 and X-2 having the following compositions are excluded. liquid crystal medium. 【Chemistry 1】 (In the formula, R Ｌ represents a linear or branched alkyl or alkoxy group having H and 1 to 15 C atoms, provided that these groups contain one or more CH ２ The groups are arranged so that the oxygen atoms are not directly bonded to each other, 【Chemistry 2】 -C≡C-, -CF ２ O-, -OCF ２ -, -CH=CH-, -O-, -CO-O- or -O-CO- may be substituted, provided that one or more H atoms are replaced by halogens. X Ｌ F, Cl, CN, CHF ２ CF ３ or OCF ３ This represents, Y Ｌ represents H, F, Cl or CH ３ .) 【Transformation 3】 (In the formula, R ２Ａ , R ２Ｂ , R ２Ｃ and R ２Ｄ Each represents an alkyl or alkenyl group having H and up to 15 C atoms, and the group is either unsubstituted or CN or CF ３ It is monosubstituted with or at least monosubstituted with a halogen, and in addition, one or more CH groups are present in these groups. ２ The group is formed so that the oxygen atoms are not directly bonded to each other, -O-, -S-, 【Chemistry 4】 -C≡C-, -CF ２ O-, -OCF ２ -, -CO-O- or -O-CO- may be used as substitutes. L １ ~L ４ These are F, Cl, and CF, which are independent of each other. ３ or CHF ２ This represents, Y is H, F, Cl, CF ３ CHF ２ or CH ３ This represents, Z ２ Z ２Ｂ and Z ２Ｄ Each of them is independently bonded to the other by a single bond, -CH ２ CH ２ -, -CH=CH-, -CF ２ O-, -OCF ２ -ien-CH ２ O-, -OCH ２ -, -COO-, -OCO-, -C ２ F ４ -, -CF=CF- or -CH=CHCH ２ Represents O-, (O) represents an oxygen atom or a single bond. p represents 0, 1, or 2. q represents 0 or 1, and (v represents 1, 2, 3, 4, 5, or 6.) Table 1 Table 2 (However, the structures of the compounds contained in mixtures X-1 and X-2 are indicated by acronyms, and their conversion to chemical formulas is performed according to Tables A to C described in the specification.)

2. The medium according to claim 1, comprising one or more compounds of formula I selected from the group of compounds of formula I-1 and I-2. 【Transformation 5】 (In the ceremony R and L1 each represent an alkyl or alkenyl group having 1 to 7 carbon atoms or 2 to 7 carbon atoms, and the CH2 group in the group may be replaced with cyclopropane-1,2-diyl.

3. The medium according to claim 1 or 2, wherein the total concentration of one or more compounds of formula I is in the range of 0.1% by weight to 10% by weight.

4. The medium according to any one of claims 1 to 3, wherein the total concentration of one or more compounds of formula IIA and IIB is in the range of 30% to 45% by weight.

5. A medium according to any one of claims 1 to 4, comprising one or more compounds of formula III. 【Transformation 6】 (In the formula, R １１ and R １２ Each represents an alkyl or alkoxy group having H and 1 to 15 C atoms independently of each other, provided that these groups have one or more CH ２ The groups are arranged so that the oxygen atoms are not directly bonded to each other, 【Transformation 7】 -C≡C-, -CF ２ O-, -OCF ２ -, -CH=CH- may be replaced with -O-, -CO-O- or -O-CO-, and one or more H atoms may be replaced with halogens. A １ Each of them appeared independently, a) One or two non-adjacent CHs ２ A 1,4-cyclohexenylene or 1,4-cyclohexylene group in which the group may be replaced by -O- or -S-, b) A 1,4-phenylene group in which one or two CH groups may be replaced by N, c) Groups from the group spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, phenanthrene-2,7-diyl and fluorene-2,7-diyl This represents, However, groups a), b), and c) may be monosubstituted or polysubstituted with halogen atoms. n is 0, 1, or 2. Z １ In each instance, -CO-O-, -O-CO-, and -CF appear independently. ２ O-, -OCF ２ -ien-CH ２ O-, -OCH ２ -ien-CH ２ -ien-CH ２ CH ２ -, - (CH ２ ) ４ -, -CH=CH-CH ２ O-, -C ２ F ４ -ien-CH ２ CF ２ -, -CF ２ CH ２ -, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C- or single bond, and L １１ and L １２ These are F, Cl, and CF, which are independent of each other. ３ or CHF ２ Represents, and (W represents O or S.)

6. A medium according to any one of claims 1 to 5, comprising one or more compounds of formula IV. 【Transformation 8】 (In the formula, R ４１ This represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms, and R ４２ (This represents an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms.)

7. The medium according to any one of claims 1 to 6, comprising one or more compounds selected from the group of compounds of the following formula. 【Chemistry 9】

8. The medium according to any one of claims 1 to 7, comprising one or more compounds of formula IVb-1 to IVb-3. 【Chemistry 10】 (In the formula, alkyl and alkyl ＊ Each of these represents an alkyl group having 1 to 6 carbon atoms independently of each other, and alkenyl and alkenyl ＊ Each of these represents an alkenyl having 2 to 6 carbon atoms independently of each other.

9. A medium according to any one of claims 1 to 8, comprising one or more compounds of formula V. 【Chemistry 11】 (In the formula, R ５１ , R ５２ This represents an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkoxyalkyl group, alkenyl group, or alkenyloxy group, each having 2 to 7 carbon atoms. 【Chemistry 12】 This represents, Z ５１ Z ５２ Each of them is independently of the other -CH ２ -CH ２ -ien-CH ２ -O-, -CH=CH-, -C≡C-, -COO- or single bond, and n is either 1 or 2.

10. A medium according to any one of claims 1 to 9, comprising a chiral dopant.

11. A medium according to any one of claims 1 to 10, comprising one or more polymerizable compounds of formula P. 【Chemistry 13】 (In the formula, P represents a polymerizable group, Sp represents a spacer group or single bond. A １ A ２ These are identical or distinct groups representing aromatic, heteroaromatic, alicyclic, or heterocyclic groups, and the group may include a fused ring, and the group is unsubstituted or monosubstituted or polysubstituted with L. L represents F, Cl, -CN, P-Sp-, or a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, provided that one or more non-adjacent CH groups are present. ２ The group may be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- such that the O and / or S atoms are not directly linked to each other, except that one or more H atoms may be replaced with P-Sp-, F, or Cl. Z １ represents -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -OCH ２ -, -CH ２ O-, -SCH ２ -, -CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -(CH ２ ) ｎ１ -, -CF ２ CH ２ -, -CH ２ CF ２ -, -(CF ２ ) ｎ１ -, -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH-, -CH ２ -CH ２ -CO-O-, -O-CO-CH ２ -CH ２ -, -CR ０ R ００ - or represents a single bond, R ０ , R ００ These represent alkyl groups having the same or different H or 1 to 12 C atoms. R represents H, L, or P-Sp-, z is 0, 1, 2, or 3. n1 is 1, 2, 3, or 4.

12. The LC medium according to claim 11, wherein the polymerizable compound of formula P is polymerized.

13. A method for preparing an LC medium according to any one of claims 1 to 12, A method comprising the step of mixing one or more compounds selected from the group consisting of formulas I, IIA, IIB, IIC, and IID of claim 1 with one or more mesogens or liquid crystal compounds other than the compounds of formulas I, IIA, IIB, IIC, and IID of claim 1.

14. An LC display comprising the medium described in any one of claims 1 to 12.

15. The LC display according to claim 14, which is a PSA display.

16. The LC display according to claim 15, which is a PS-VA, PS-IPS, PS-FFS, PS-UB-FFS, polymerization-stabilized SA-VA, or polymerization-stabilized SA-FFS display.

17. The LC display according to claim 14, which is a VA, IPS, U-IPS, FFS, UB-FFS, SA-FFS, or SA-VA display.

18. Use of a liquid crystal medium according to any one of claims 1 to 12 in an electro-optical display.

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